Name: 533-67-5|(3S,4R)-3,4,5-Trihydroxypentanal|98%
Brand: Ambeed
SKU: A358856
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1
[ 533-67-5 ]
[ 13942-76-2 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium borate
	With sodium borate; lithium hydroxide monohydrate
	With ethanol; nickel

	With sodium tetrahydridoborate In methanol for 4h;
	With sodium tetrahydridoborate In ethanol for 1h; Ambient temperature;
	With xylose reductase from yeast Candida intermedia; NADPH In phosphate buffer at 25℃;
	With sodium borohydride In ethanol; glacial acetic acid	267 2-Deoxy-D-erythro-pentitol EXAMPLE 267 2-Deoxy-D-erythro-pentitol Under anhydrous conditions and an argon purge, 30.0 g of 2-deoxy-D-ribose is dissolved in 1 L of ethyl alcohol. Seven grams of sodium borohydride is added in portions at room temperature. The reaction mixture is stirred for 1-2 hours, until all bubbles disappear. The mixture is acidified with 25 ml of glacial acetic acid and the stirring continued for an additional 30 minutes. The solution is chromatographed using 180 ml of Dowex 50W-X8(H+ form) Resin (50-100 mesh) and ethyl alcohol. The filtrate is concentrated in vacuo to give 40.0 g of a thick oil. MS (EI):m/z 119(M+ -OH).
	In lithium hydroxide monohydrate; hydrogen	1 EXAMPLE 1 EXAMPLE 1 An 80 g (0.60 mole) portion of 2-deoxy-D-ribose was dissolved in 240 ml of water to form an aqueous solution into which 15 g of Raney nickel were added. The thus prepared reaction mixture in an autoclave was heated under a hydrogen pressure of 40 kg/cm2 G up to a temperature of 70° C. taking 30 minutes and kept for additional 1 hour at the same temperature and under the same hydrogen pressure. After cooling, the reaction mixture taken out of the autoclave was filtered to remove the solid catalyst and the filtrate, as combined with the washings of the solid catalyst with water, was subjected to removal of the water to give about 80 g of 2-deoxy-D-erythropentitol. The yield of the product was almost quantitative.
	In lithium hydroxide monohydrate; hydrogen	2 EXAMPLE 2 EXAMPLE 2 A 100 g (0.75 mole) portion of 2-deoxy-D-ribose was dissolved in 200 ml of water to form an aqueous solution into which 20 g of Raney nickel were added. The thus prepared reaction mixture in an autoclave was heated under a hydrogen pressure of 40 kg/cm2 G up to a temperature of 70° C. taking 30 minutes and kept for additional 1 hour at the same temperature and under the same hydrogen pressure. After cooling, the reaction mixture taken out of the autoclave was filtered to remove the solid catalyst and the filtrate, as combined with the washings of the solid catalyst with water, was subjected to removal of the water to give about 100 g of 2-deoxy-D-erythropentitol. The yield of the product was almost quantitative.
	With hydrogen In lithium hydroxide monohydrate at 70℃; for 1.5h;	38.A Example 38A(2R,3S)-pentane-1,2,3,5-tetraolWater (50 mL) and Ra-Ni, water-wet (5.03 g, 38.6 mmol) were added to (3S,4R)-3,4,5-trihydroxypentanal (25.19 g, 188 mmol) in a 300 mL SS reactor. The mixture was stirred for 1.5 hr at 70° C. under 800 psi (literature 570 psi) of Hydrogen. The 270 psi pressure drop was consistent with full conversion, and the DCI-MS showed only ions for the expected product. The mixture was filtered through a nylon membrane, the reactor was rinsed with water, and the filtrate was concentrated and afforded 25.8 g of the title compound. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.36-1.48 (m, 1H) 1.66-1.77 (m, 1H) 3.20-3.27 (m, 1H) 3.33 (dd, J=11.66, 6.14 Hz, 1H) 3.38-3.59 (m, 4H) 4.25-4.33 (m, 3H) 4.40 (d, J=5.22 Hz, 1H); MS (ESI) m/z 137 (M+H)+.
	With hydrogen In lithium hydroxide monohydrate at 70℃;	22A Water (50 mL) and Ra-Ni, water-wet (5.03 g, 38.6 mmol) were added to (3S,4R)-3,4,5-trihydroxypentanal (25.19 g, 188 mmol) in a 300 mL stainless steel reactor. The mixture was stirred for 1.5 hr at 70° C. under 800 psi (literature 570 psi) of hydrogen. The 270 psi pressure drop was consistent with full conversion, and the DCI-MS showed only ions for the expected product. The mixture was filtered through a nylon membrane, the reactor was rinsed with water, and the filtrate was concentrated and afforded 25.8 g of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36-1.48 (m, 1H) 1.66-1.77 (m, 1H) 3.20-3.27 (m, 1H) 3.33 (dd, J=11.66, 6.14 Hz, 1H) 3.38-3.59 (m, 4H) 4.25-4.33 (m, 3H) 4.40 (d, J=5.22 Hz, 1H); MS (ESI) m/z 137 (M+H)+
	With hydrogen In lithium hydroxide monohydrate at 70℃; for 1.5h; SS reactor;	38.38A Example 38; (E)-N-(5-tert-butyl-2-(((2R,3R)-3-fluorotetrahydro furan-2-yl)methyl)-1-methyl-1H-pyrazol-3(2H)-ylidene)-2-methoxy-5-(trifluoromethyl)benzamide; Example 38A; (2R,3S)-pentane-1,2,3,5-tetraol; Water (50 mL) and Ra-Ni, water-wet (5.03 g, 38.6 mmol) were added to (3S,4R)-3,4,5-trihydroxypentanal (25.19 g, 188 mmol) in a 300 mL SS reactor. The mixture was stirred for 1.5 hr at 70° C. under 800 psi of hydrogen. The mixture was filtered through a nylon membrane, the reactor was rinsed with water, and the filtrate was concentrated and afforded 25.8 g of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36-1.48 (m, 1H) 1.66-1.77 (m, 1H) 3.20-3.27 (m, 1H) 3.33 (dd, J=11.66, 6.14 Hz, 1H) 3.38-3.59 (m, 4H) 4.25-4.33 (m, 3H) 4.40 (d, J=5.22 Hz, 1H); MS (ESI) m/z 137 (M+H)+.
	With hydrogen In lithium hydroxide monohydrate at 70℃;	22A Water (50 mL) and Ra-Ni, water-wet (5.03 g, 38.6 mmol) were added to (3S,4R)-3,4,5-trihydroxypentanal (25.19 g, 188 mmol) in a 300 mL stainless steel reactor. The mixture was stirred for 1.5 hr at 70° C. under 800 psi (literature 570 psi) of hydrogen. The 270 psi pressure drop was consistent with full conversion, and the DCI-MS showed only ions for the expected product. The mixture was filtered through a nylon membrane, the reactor was rinsed with water, and the filtrate was concentrated and afforded 25.8 g of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36-1.48 (m, 1H) 1.66-1.77 (m, 1H) 3.20-3.27 (m, 1H) 3.33 (dd, J=11.66, 6.14 Hz, 1H) 3.38-3.59 (m, 4H) 4.25-4.33 (m, 3H) 4.40 (d, J=5.22 Hz, 1H); MS (ESI) m/z 137 (M+H)+

Reference： [1]Hardegger et al. [Helvetica Chimica Acta, 1957, vol. 40, p. 1819,1822]
[2]David; Jaymond [Bulletin de la Societe Chimique de France, 1959, p. 157]
[3]David; Jaymond [Bulletin de la Societe Chimique de France, 1959, p. 157]
[4]Holy [Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 10, p. 2786 - 2805]
[5]Tymiak,A.A.; Rinehart,K.L. [Journal of the American Chemical Society, 1983, vol. 105, p. 7396]
[6]Nidetzky, Bernd; Brueggler, Kaspar; Kratzer, Regina; Mayr, Peter [Journal of Agricultural and Food Chemistry, 2003, vol. 51, # 27, p. 7930 - 7935]
[7]Current Patent Assignee: PFIZER INC - US5602118, 1997, A
[8]Current Patent Assignee: NIKKO RICA - US5789572, 1998, A
[9]Current Patent Assignee: NIKKO RICA - US5789572, 1998, A
[10]Current Patent Assignee: ABBVIE INC - US2009/105306, 2009, A1 Location in patent: Page/Page column 36
[11]Current Patent Assignee: ABBVIE INC Location in patent: Page/Page column 31; 32 ABBOTT LABORATORIES; ABBOTT LABORATORIES; Carroll, William A.; Dart, Michael J.; Frost, Jennifer M.; Latshaw, Steven P.; Kolasa, Teodozyj; Li, Tongmei; Peddi, Sridhar; Liu, Bo; Perez-Medrano, Arturo; Patel, Meena; Wang, Xueqing; Nelson, Derek W.
[12]Current Patent Assignee: ABBVIE INC - US2010/249129, 2010, A1 Location in patent: Page/Page column 39
[13]Current Patent Assignee: ABBVIE INC Location in patent: Page/Page column 31; 32 ABBOTT LABORATORIES; ABBOTT LABORATORIES; Carroll, William A.; Dart, Michael J.; Frost, Jennifer M.; Latshaw, Steven P.; Kolasa, Teodozyj; Li, Tongmei; Peddi, Sridhar; Liu, Bo; Perez-Medrano, Arturo; Patel, Meena; Wang, Xueqing; Nelson, Derek W.

2
[ 533-67-5 ]
1-O-methyl-2-deoxy-D-ribofuranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; methanol
	With pyridine; hydrogenchloride; sodium bicarbonate In methanol; toluene	R.2 Synthesis of methyl 2-deoxy-D-erythro-pentofuranoside Reference Example 2 Synthesis of methyl 2-deoxy-D-erythro-pentofuranoside In 1.1 liters of methanol, 52 g of 2-deoxy-D-erythro-pentose was dissolved, and 3.8 ml of 1 M hydrochloric acid solution in methanol was added at room temperature, followed by stirring the resulting solution at room temperature for 1 hour. To the reaction mixture, 1 g of sodium hydrogen carbonate was added and the resultant was concentrated after confirming that the solution was weakly basic. To the residue, 100 ml of toluene and 100 ml of pyridine were added to dissolve the residue and the resultant was concentrated. This operation was repeated totally twice to completely remove methanol. The thus obtained crude methyl 2-deoxy-α-D-erythro-pentofuranoside was used in the subsequent step without purification.

Reference： [1]Deriaz et al. [Journal of the Chemical Society, 1949, p. 2836,2839]
[2]Current Patent Assignee: MITSUI CHEMICALS,INC. - EP635517, 1995, A1

3
[ 533-67-5 ]
[ 75-08-1 ]
[ 115214-11-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With hydrogenchloride at 0℃; for 1h; Inert atmosphere;
71%	With hydrogenchloride at 20℃; for 3h;
	With hydrogenchloride

With hydrogenchloride

Reference： [1]Song, Wei-Syun; Liu, Si-Xian; Chang, Che-Chien [Journal of Organic Chemistry, 2018, vol. 83, # 24, p. 14923 - 14932]
[2]Tungen, Jørn Eivind; Gerstmann, Lisa; Vik, Anders; De Matteis, Roberta; Colas, Romain Alexandre; Dalli, Jesmond; Chiang, Nan; Serhan, Charles Nicholas; Kalesse, Markus; Hansen, Trond Vidar [Chemistry - A European Journal, 2019, vol. 25, # 6, p. 1476 - 1480]
[3]Zinner et al. [Chemische Berichte, 1957, vol. 90, p. 2688,2691]
[4]Park; Piatak; Peterson; Clark [Canadian Journal of Chemistry, 1992, vol. 70, # 6, p. 1662 - 1665]

4
[ 533-67-5 ]
[ 116-11-0 ]
3,4-O-isopropylidene-2-deoxy-D-ribose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridinium p-toluenesulfonate 1.) ethyl acetate, 23 deg C, 3 h, 2.) pH 5.5 phosphate buffer, 23 deg C, 10 min; Yield given. Multistep reaction;
	With pyridinium p-toluenesulfonate In ethyl acetate for 3h; Ambient temperature;
	In ethyl acetate	3 2-deoxy-D-ribose is converted to the acetonide-protected lactol 10 by treatment with 2-methoxypropene and catalytic pyridinium p-toluenesulfonate (PPTS) in ethyl acetate. Wittig reaction with Ph3PCHCO2Et in THF in the presence of catalytic benzoic acid affords enoate 11, which is reduced to 12 under a hydrogen atmosphere in the presence of catalytic Pd/C in ethanol. Deprotection of 12 using 0.1 N HCl in ethanol for 5 minutes, followed by quenching with aqueous NaHCO3, affords 8 after silica gel chromatographic purification.

With pyridinium p-toluenesulfonate In ethyl acetate

3 EXAMPLE 3; Synthesis of Compound 8; 2-deoxy-D-ribose is converted to the acetonide-protected lactol 10 by treatment with 2-methoxypropene and catalytic pyridinium p-toluenesulfonate (PPTS) in ethyl acetate. Wittig reaction with Ph3PCHCO2Et in THF in the presence of catalytic benzoic acid affords enoate 11, which is reduced to 12 under a hydrogen atmosphere in the presence of catalytic Pd/C in ethanol. Deprotection of 12 using 0.1 N HCl in ethanol for 5 minutes, followed by quenching with aqueous NaHCO3, affords 8 after silica gel chromatographic purification.

Reference： [1]Corey; Marfat; Goto; Brion [Journal of the American Chemical Society, 1980, vol. 102, # 27, p. 7984 - 7985]
[2]Yadav, J. S.; Vadapalli, Prahlad [Tetrahedron Letters, 1994, vol. 35, # 4, p. 641 - 644]
[3]Current Patent Assignee: NOVARTIS AG; ALCON, INC.; Novartis (w/o Sandoz) - US2006/99248, 2006, A1 Location in patent: Page/Page column 6
[4]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2006/154981, 2006, A1 Location in patent: Page/Page column 3-4

5
[ 533-67-5 ]
[ 113-24-6 ]
[ 128726-71-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium dihydrogenphosphate; sodium azide; diothiothreitol at 30℃; for 72h; KDO aldolase (EC 4.1.2.23) from Aureobacterium barkerei strain KDO-37-2 (ATCC 49977);

Reference： [1]Sugai, Takeshi; Shen, Gwo-Jenn; Ichikawa, Yoshitaka; Wong, Chi-Huey [Journal of the American Chemical Society, 1993, vol. 115, # 2, p. 413 - 421]

6
[ 89534-51-0 ]
[ 5284-18-4 ]
[ 533-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	With ozone In methanol at -78℃; for 0.75h; Title compound not separated from byproducts;

Reference： [1]Heathcock, Clayton H.; Young, Steven D.; Hagen, James P.; Pirrung, Michael C.; White, Charles T.; VanDerveer, Don [Journal of Organic Chemistry, 1980, vol. 45, # 19, p. 3846 - 3856]

7
[ 533-67-5 ]
[ 108-03-2 ]
[ 77180-65-5 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium In methanol for 24h;

Reference： [1]Wickremesinghe, L. Kirthi G.; Slessor, Keith N. [Carbohydrate Research, 1981, vol. 88, p. 153 - 157]

8
[ 87616-31-7 ]
[ 533-67-5 ]
[ 76945-38-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With pH 10.5 In water at 90℃;

Reference： [1]Saito,I.; Sugiyama,H.; Matsuura,T. [Journal of the American Chemical Society, 1983, vol. 105, p. 6989]

9
[ 533-67-5 ]
[ 21204-67-1 ]
[ 78606-78-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	In 1,2-dimethoxyethane for 5h; Heating;

Reference： [1]Corey, E. J.; Marfat, Anthony; Munroe, John; Kim, Kwan Soo; Hopkins, Paul B.; Brion, Francis [Tetrahedron Letters, 1981, vol. 22, p. 1077 - 1080]

10
[ 533-67-5 ]
[ 59-46-1 ]
[ 150-13-0 ]
4-((4S,5R)-4,5-Dihydroxy-tetrahydro-pyran-2-ylamino)-benzoic acid 2-diethylamino-ethyl ester [ No CAS ]
2-Deoxy-N-p-carboxyphenyl-β-D-ribopyranosylamine [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 2495 - 2503

11
[ 533-67-5 ]
[ 31735-35-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine In ethanol; water for 1h; Ambient temperature;
	With hydroxylamine In ethanol; water at 20℃; for 1h;

Reference： [1]Fascio, Mirta L.; D'Accorso, Norma B. [Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1573 - 1577]
[2]Fascio; D'Accorso [Synthetic Communications, 2001, vol. 31, # 12, p. 1913 - 1920]

12
[ 533-67-5 ]
[ 305-15-7 ]
2-deoxyribose (2,5-dichlorophenyl)hydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In methanol Heating;

Reference： [1]Spencer, Roxanne P.; Yu, Hye Kyung Bae; Cavallaro, Cullen L.; Schwartz, Jeffrey [Journal of Organic Chemistry, 1997, vol. 62, p. 4507 - 4509]

13
[ 67-56-1 ]
[ 533-67-5 ]
(2R,3S)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride
100%	With hydrogenchloride
98%	With hydrogenchloride at 0 - 20℃;	1 Example 1 Preparation of 1-O-methyl-2-deoxy-D-ribofuranose (Compound IV) In a 5L reaction bottle,Add 2L of 1% HCl in methanol,Cool to 0 to 5 ° C,Add 100 g (755.55 mmol) of 2-deoxy-D-ribose and naturally return to room temperature.After 1 to 2 hours of reaction,TLC detection of the raw material 2-deoxy-D-ribose reaction completely(Dichloromethane: methanol = 8:1 V/V).Add about 30 mL of saturated sodium bicarbonate solution,Adjust PH=8 or so,Filtration and concentration of solvent under reduced pressure, adding 200 toluene,Concentrated and dried under reduced pressure,Continue to add 200 toluene,Concentrated under reduced pressure to obtain 108 g of a slurry(Yield: 98%),Used directly in the next step.

97.7%	With hydrogenchloride at 20℃; for 2.5h;	1-2 Example 2 In a 500mL three-necked flask, add 20g 2-deoxy-D-ribose and 300mL anhydrous methanol, stir at 20°C until the solid is completely dissolved, and the system is a slightly yellow transparent solution; add 1mL 0.1% hydrochloric acid-methanol solution dropwise through a constant pressure funnel . After the dropwise addition was completed, the mixture was stirred for 2.5 hours. TLC detected that the reaction was completed, 0.5 g of calcium carbonate was added, and stirring was continued for 30 minutes. After suction filtration, the solvent was evaporated to dryness under reduced pressure to obtain 21.6 g of an oily intermediate I with a yield of 97.7%.
96%	With acetyl chloride for 1h; Inert atmosphere;
	With hydrogenchloride In 1,4-dioxane for 0.25h; Ambient temperature;
13.00 g	With acetyl chloride at 20℃; for 0.25h;
	With hydrogenchloride
	With sulfuric acid at 0℃; for 1h;
	With triethylamine; acetyl chloride at 7℃; for 1.66667h; Inert atmosphere;	1 Preparation of 1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-alpha-D-ribofuranosyl-chloride Example 1 Preparation of 1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-alpha-D-ribofuranosyl-chloride Into a 4-neck 3 L RB flask that was dried under a nitrogen stream was charged 100 g of 2-deoxy-D-ribose and anhydrous methanol (500 mL). The mixture was cooled to 7° C. Under mixing, acetyl chloride (1.56 g) was added through a syringe. After 1.5 hr at this temperature triethylamine (4.24 g) was added and mixing was continued for 10 min. to yield 1-O-methyl-2-deoxy-D-ribofuranose. Methanol was removed under vacuum using a warm water bath (40° C.). Residual methanol was removed by adding dioxane (189 g) then removing the residual methanol under vacuum using a warm water bath. Into the 1-O-methyl-2-deoxy-D-ribofuranose was added dioxane (1.8 L), 4-dimethylaminopyridine (DMAP, 3 g), and triethylamine (171 g). Then p-chlorobenzoyl chloride (268.5 g) was added slowly while the temperature was maintained at 15-18° C. No aqueous work-up was required. The slurry was mixed at room temperature overnight then vacuum filtered into a 5-L 4-neck RB flask. The cake was rinsed with dioxane (0.2 L); and the rinse was combined with the filtrate. Acetic acid was added (0.84 kg) to the rinse/filtrate mixture, followed by the addition of acetyl chloride (14.1 g). HCl gas (330 g) was fed while maintaining temperature between 12-18° C. Precipitate started to form and the slurry was mixed for an additional 20 minutes after HCl addition was complete. Hexane was added (0.5 L) and the product was collected via vacuum filtration. After rinsing with hexane (0.3 L) the product was vacuum-dried to give 144 g of 1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-alpha-D-ribofuranosyl-chloride as white solid for use in Examples 4 and 5.
	Stage #1: methanol; 2-Deoxy-D-ribose With hydrogenchloride In diethyl ether at 20℃; Stage #2: With sodium (meta)periodate In methanol; diethyl ether at 20℃; for 28h;	1 Example 1 - Formation of methyl-2-deoxyriboside and destruction of methyl-2- deoxyribopyranoside by oxidation; 2-Deoxy-D-ribose (50 g, 0.373 mol) was charged into a 1L 3-necked round bottom flask followed by methanol (500 ml_). The mixture was stirred until dissolution. A solution of HCI in diethyl ether (5.0 mL, 0.005 mol) was added in one portion and the resulting mixture was stirred at room temperature overnight. Upon completion the batch was quenched by addition of solid sodium bicarbonate (7.0 g, 0.08 mol) and the resulting mixture was stirred for 30 min. The reaction mixture was filtered through a fritted funnel and the solid on the filter was washed with methanol. The wash filtrate was combined with the main product filtrate. The filtrate was transferred into a reaction flask via polyethylene tubing using vacuum. About 1.7 wt% of water of reaction was present at this point, relative to total solvent. Finely powdered sodium periodate ( 12.0 g, 0.056 mol) was charged into the reaction flask in portions. The resulting suspension was stirred at room temperature for 6h and then sampled for in-process GC testing. GC analysis indicated approximately 0.73 % of MDRP in the reaction mixture.The batch was continuously stirred at room temperature for additional 18h and GC analysis was repeated. It indicated the presence of about 0.5 % of MDRP in the reaction mixture. An additional solid sodium periodate ( 1.6 g, 0.007 mol) was charged and the resulting mixture was stirred at room temperature for 4 h. GC testing indicated no detectable MDRP in the reaction mixture. To quench the reaction, solid sodium bicarbonate (12.0 g, 0.149 mol) was charged to the reaction mixture and stirring was continued for another 15 min. The reaction mixture was filtered through a fritted funnel and the filtrate was concentrated in a rotary evaporator until no more condensate was observed. The resulting oil was diluted with acetonitrile (500 mL) and then filtered through a Celite pad . The filtrate was concentrated on a rotary evaporator to give the product (55.4 g, 106 % yield).
	With hydrogenchloride In water monomer at 20℃; for 0.5h;	1.1 Step 1 (cyclization) In 10L reaction flask was added hydrogen chloride containing 0.1% (w / v) in methanol (7.6L), followed by addition of 2-deoxy-ribose -D- (0.380kg, 2.83mol), the reaction was stirred vigorously at room temperature for 30min, TLC detection complete control of the reaction, dry pyridine was added, controlling pH of 7.5-8.0.Concentrated under reduced pressure below 70 deg.] C to give a yellow viscous product of Intermediate 2, was used directly in the next reaction.
	With hydrogenchloride In diethyl ether at 20℃; for 3h;

Reference： [1]Location in patent: scheme or table Schomaker, Jennifer M.; Borhan, Babak [Journal of the American Chemical Society, 2008, vol. 130, # 37, p. 12228 - 12229]
[2]Duca, Maria; Malnuit, Vincent; Barbault, Florent; Benhida, Rachid [Chemical Communications, 2010, vol. 46, # 33, p. 6162 - 6164]
[3]Current Patent Assignee: PARLING SHANGHAI PHARMATECH - CN110028537, 2019, A Location in patent: Paragraph 0044-0045
[4]Current Patent Assignee: CHEMVON BIOTECHNOLOGY SHANGHAI CO LTD - CN114230601, 2022, A Location in patent: Paragraph 0032-0034
[5]Ghosh, Titli; Mukherji, Ananya; Srivastava, Hemant Kumar; Kancharla, Pavan K. [Organic and Biomolecular Chemistry, 2018, vol. 16, # 16, p. 2870 - 2875]
[6]Chin, Tsung-Mei; Huang, Liang-Kuen; Kan, Lou-Sing [Journal of the Chinese Chemical Society, 1997, vol. 44, # 4, p. 413 - 416]
[7]Birk, Claudia; Voss, Juergen; Wirsching, Joern [Carbohydrate Research, 1997, vol. 304, # 3-4, p. 239 - 247]
[8]Takahashi, Takashi; Hirose, Yoichiro; Iwamoto, Hajime; Doi, Takayuki [Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 5742 - 5743]
[9]Zammit, Steven C.; Ferro, Vito; Hammond, Edward; Rizzacasa, Mark A. [Organic and Biomolecular Chemistry, 2007, vol. 5, # 17, p. 2826 - 2834]
[10]Current Patent Assignee: ALBEMARLE CORP - US2010/249394, 2010, A1 Location in patent: Page/Page column 4
[11]Current Patent Assignee: JOHNSON MATTHEY PLC - WO2012/71508, 2012, A1 Location in patent: Page/Page column 5-6; 8
[12]Current Patent Assignee: JIANGSU MINGTAI INVESTMENT GROUP LTD - CN102827224, 2016, B Location in patent: Paragraph 0041; 0042; 0043
[13]Shiozaki, Yoko; Sakurai, Shunya; Sakamoto, Ryu; Matsumoto, Akira; Maruoka, Keiji [Chemistry - An Asian Journal, 2020, vol. 15, # 5, p. 573 - 576]

14
[ 533-67-5 ]
[ 86302-43-4 ]
(Z)-(5S,6R)-5,6,7-Trihydroxy-hept-2-enoic acid tert-butyl ester [ No CAS ]
[ 208036-02-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	In tetrahydrofuran at 60℃; for 6h; Yields of byproduct given;

Reference： [1]Bennett, Sharon M.; Biboutou, Raphinos Kouya; Zhou, Zhihong; Pion, Robert [Tetrahedron, 1998, vol. 54, # 19, p. 4761 - 4786]

15
[ 533-67-5 ]
[ 7393-43-3 ]
[ 195196-44-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(II) bis(trifluoromethanesulfonate) In ethanol; water; toluene at 70℃; for 5h;

Reference： [1]Kobayashi, Shu; Nagayama, Satoshi; Busujima, Tsuyoshi [Chemistry Letters, 1997, # 9, p. 959 - 960]

16
[ 533-67-5 ]
[ 593-51-1 ]
[ 52160-51-7 ]
[ 81263-87-8 ]
N,N',N''-trimethyltripyrrane [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,1998,vol. 46,p. 104 - 110

Yield	Reaction Conditions	Operation in experiment
	With ethanol; palladium Hydrogenation_.und Behandlung des Reaktionsprodukts mit wss.-aethanol.Natronlauge und anschliessend mit wss.Schwefelsaeure;

18
[ 14431-43-7 ]
[ 533-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 120℃; Behandeln der vom Calciumhydroxid befreiten Reaktionsloesung mit wss. Wasserstoffperoxid unter Zusatz von Eisen(II)-sulfat und Bariumacetat;

Reference： [1]Diehl; Flechter [Archives of Biochemistry, 1958, vol. 78, p. 386,388][Biochemical Preparations, 1961, vol. 8, p. 49]

19
[ 533-67-5 ]
[ 1099-45-2 ]
[ 79308-40-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	In tetrahydrofuran at 90℃;
91%	In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Salari; Biboutou; Bennett [Tetrahedron, 2000, vol. 56, # 35, p. 6385 - 6400]

20
[ 533-67-5 ]
2-deoxy-D-ribonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With phenoxyamine hydrochloride In aq. phosphate buffer; water-d2 at 20℃; for 16h;	1.1.3 General procedure for the formation of cyanohydrins General procedure: To a 7mL vial was added reducing sugar (1 equiv), O-phenylhydroxylamine hydrochloride (H2NOPh) (1.2 equiv), and 0.2M sodium phosphate pD 7.25 to the final concentration of 0.1M. The reaction was stirred at room temperature until the oxime intermediates were disappeared (monitored by 1H NMR). Then, the reaction mixture was transferred into a separatory funnel and washed with diethyl ether for 10 times. The remaining aqueous solution was evaporated to dryness. Ethanol was added to the solid residue to extract the product from the phosphate salt. The phosphate salt residues in the ethanol solution were removed by centrifugation. The solvent was evaporated to obtain the desired product.
	With ammonia; iodine In water at 20℃; for 0.5h;
	With ammonium hydroxide; ammonium cerium(IV) nitrate at 0℃; for 0.25h;

Reference： [1]Cheewawisuttichai, Thamrongsak; Hurst, Robert D.; Brichacek, Matthew [Carbohydrate Research, 2021, vol. 502]
[2]Talukdar, Sanjay; Hsu, Jue-Liang; Chou, Tzu-Chi; Fang, Jim-Min [Tetrahedron Letters, 2001, vol. 42, # 6, p. 1103 - 1105]
[3]Bandgar; Makone [Synlett, 2003, # 2, p. 262 - 264]

21
[ 533-67-5 ]
[ 453-17-8 ]
[ 75-07-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 43 - 52

22
[ 533-67-5 ]
[ 108-24-7 ]
[ 49560-18-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With ammonium hydroxide; N-Bromosuccinimide at 0℃; for 0.25h;

Reference： [1]Bandgar; Makone [Synthetic Communications, 2006, vol. 36, # 10, p. 1347 - 1352]

23
[ 533-67-5 ]
[ 100-51-6 ]
[ 418760-06-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With dimethylsilicon dichloride at 25℃;

Reference： [1]Haraguchi, Kazuhiro; Delaney, Michael O.; Wiederholt, Carissa J.; Sambandam, Aruna; Hantosi, Zsolt; Greenberg, Marc M. [Journal of the American Chemical Society, 2002, vol. 124, # 13, p. 3263 - 3269]

24
[ 461015-77-0 ]
[ 533-67-5 ]
3-Isobutyl-1-propyl-9-((3S,4R)-3,4,5-trihydroxy-pentyl)-1,4,9-triaza-spiro[5.5]undecane-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 20℃; for 36h;

Reference： [1]Habashita, Hiromu; Kokubo, Masaya; Hamano, Shin-ichi; Hamanaka, Nobuyuki; Toda, Masaaki; Shibayama, Shiro; Tada, Hideaki; Sagawa, Kenji; Fukushima, Daikichi; Maeda, Kenji; Mitsuya, Hiroaki [Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4145 - 4152]

25
[ 533-67-5 ]
[ 103-49-1 ]
[ 910658-48-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: 2-Deoxy-D-ribose; dibenzylamine In dichloromethane for 24h; Stage #2: With sodium tetrahydroborate In dichloromethane at 0 - 20℃; for 3h;

Reference： [1]Lallana, Enrique; Freire, Felix; Seco, Jose Manuel; Quinoa, Emilio; Riguera, Ricardo [Organic Letters, 2006, vol. 8, # 20, p. 4449 - 4452]

26
[ 533-67-5 ]
4-(2-hydroxy-4-pentenyl)-2,2-dimethyl-1,3-dioxan-5-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂SO₄ / 1.5 h / 25 °C 2: 1.35 g / p-TsOH / 12 h / 25 °C 3: 98 percent / Et₂Zn; n-Bu₃P / Pd(OAc)2 / toluene; hexane / 3 h / 25 °C

Reference： [1]Shimizu, Masamichi; Kimura, Masanari; Tamaru, Yoshinao [Chemistry - A European Journal, 2005, vol. 11, # 22, p. 6629 - 6642]

27
[ 533-67-5 ]
4-(2-hydroxy-3-phenyl-4-pentenyl)-2,2-dimethyl-1,3-dioxan-5-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂SO₄ / 25 °C 2: p-TsOH / 25 °C 3: 98 percent / Et₂Zn; n-Bu₃P / Pd(OAc)2 / toluene; hexane / 5 h / 25 °C

Reference： [1]Shimizu, Masamichi; Kimura, Masanari; Tamaru, Yoshinao [Chemistry - A European Journal, 2005, vol. 11, # 22, p. 6629 - 6642]

28
[ 533-67-5 ]
(2R,3S)-1-triphenylmethoxy-7-octene-2,3,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂SO₄ / 1.5 h / 25 °C 2: 4.57 g / Et₃N / CH₂Cl₂ / 21 h / 25 °C 3: 76 percent / Et₂Zn; n-Bu₃P / Pd(OAc)2 / toluene; hexane / 1 h / 25 °C

Reference： [1]Shimizu, Masamichi; Kimura, Masanari; Tamaru, Yoshinao [Chemistry - A European Journal, 2005, vol. 11, # 22, p. 6629 - 6642]

29
[ 533-67-5 ]
(2R,3S)-6-phenyl-1-triphenylmethoxy-7-octene-2,3,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂SO₄ / 25 °C 2: Et₃N / CH₂Cl₂ / 25 °C 3: 49 percent / Et₂Zn; n-Bu₃P / Pd(OAc)2 / toluene; hexane / 5 h / 25 °C

Reference： [1]Shimizu, Masamichi; Kimura, Masanari; Tamaru, Yoshinao [Chemistry - A European Journal, 2005, vol. 11, # 22, p. 6629 - 6642]

30
[ 533-67-5 ]
(4aS,9aR)-6,6,8,8-Tetraisopropyl-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocyclohepten-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76 percent / dichlorodimethysilane / 25 °C 2: imidazole / pyridine 3: H₂ / Pd/C / ethyl acetate / 760.05 Torr

Reference： [1]Haraguchi, Kazuhiro; Delaney, Michael O.; Wiederholt, Carissa J.; Sambandam, Aruna; Hantosi, Zsolt; Greenberg, Marc M. [Journal of the American Chemical Society, 2002, vol. 124, # 13, p. 3263 - 3269]

31
[ 533-67-5 ]
(4aS,9aR)-3-Azido-6,6,8,8-tetraisopropyl-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 76 percent / dichlorodimethysilane / 25 °C 2: imidazole / pyridine 3: H₂ / Pd/C / ethyl acetate / 760.05 Torr 4: DMAP / pyridine 5: 89 percent / trimethylsilyl azide / 1,2-dichloro-ethane / 0.08 h

Reference： [1]Haraguchi, Kazuhiro; Delaney, Michael O.; Wiederholt, Carissa J.; Sambandam, Aruna; Hantosi, Zsolt; Greenberg, Marc M. [Journal of the American Chemical Society, 2002, vol. 124, # 13, p. 3263 - 3269]

32
[ 533-67-5 ]
(4aS,9aR)-6,6,8,8-Tetraisopropyl-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocyclohepten-3-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 76 percent / dichlorodimethysilane / 25 °C 2: imidazole / pyridine 3: H₂ / Pd/C / ethyl acetate / 760.05 Torr 4: DMAP / pyridine 5: 89 percent / trimethylsilyl azide / 1,2-dichloro-ethane / 0.08 h 6: H₂ / Pd/C / methanol / 1 h / 760.05 Torr

Reference： [1]Haraguchi, Kazuhiro; Delaney, Michael O.; Wiederholt, Carissa J.; Sambandam, Aruna; Hantosi, Zsolt; Greenberg, Marc M. [Journal of the American Chemical Society, 2002, vol. 124, # 13, p. 3263 - 3269]

33
[ 533-67-5 ]
[ 418760-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 76 percent / dichlorodimethysilane / 25 °C 2: imidazole / pyridine 3: H₂ / Pd/C / ethyl acetate / 760.05 Torr 4: DMAP / pyridine

Reference： [1]Haraguchi, Kazuhiro; Delaney, Michael O.; Wiederholt, Carissa J.; Sambandam, Aruna; Hantosi, Zsolt; Greenberg, Marc M. [Journal of the American Chemical Society, 2002, vol. 124, # 13, p. 3263 - 3269]

34
[ 533-67-5 ]
[ 418759-89-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 76 percent / dichlorodimethysilane / 25 °C 2: imidazole / pyridine

Reference： [1]Haraguchi, Kazuhiro; Delaney, Michael O.; Wiederholt, Carissa J.; Sambandam, Aruna; Hantosi, Zsolt; Greenberg, Marc M. [Journal of the American Chemical Society, 2002, vol. 124, # 13, p. 3263 - 3269]

35
[ 533-67-5 ]
5-Nitro-N-((4aS,9aR)-6,6,8,8-tetraisopropyl-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocyclohepten-3-yl)-pyrimidine-4,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 76 percent / dichlorodimethysilane / 25 °C 2: imidazole / pyridine 3: H₂ / Pd/C / ethyl acetate / 760.05 Torr 4: DMAP / pyridine 5: 89 percent / trimethylsilyl azide / 1,2-dichloro-ethane / 0.08 h 6: H₂ / Pd/C / methanol / 1 h / 760.05 Torr 7: 60 percent / Et₃N / dioxane / 18 h / Heating

Reference： [1]Haraguchi, Kazuhiro; Delaney, Michael O.; Wiederholt, Carissa J.; Sambandam, Aruna; Hantosi, Zsolt; Greenberg, Marc M. [Journal of the American Chemical Society, 2002, vol. 124, # 13, p. 3263 - 3269]

36
[ 533-67-5 ]
(2R,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((R)-1-hydroxy-2-methoxy-ethyl)-tetrahydro-furan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 75 percent / LiHMDS / tetrahydrofuran / 2 h / 0 °C 7: acetic acid; H₂O; tetrahydrofuran / 3 h / 0 - 20 °C
	Multi-step reaction with 7 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 75 percent / LiHMDS / tetrahydrofuran / 2 h / 0 °C 7: acetic acid; H₂O; tetrahydrofuran / 3 h / 0 - 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

37
[ 533-67-5 ]
Acetic acid (2R,3S,5S)-5-((R)-1-acetoxy-2-methoxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 75 percent / LiHMDS / tetrahydrofuran / 2 h / 0 °C 7: acetic acid; H₂O; tetrahydrofuran / 3 h / 0 - 20 °C 8: pyridine / 4 h / 60 °C
	Multi-step reaction with 8 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 75 percent / LiHMDS / tetrahydrofuran / 2 h / 0 °C 7: acetic acid; H₂O; tetrahydrofuran / 3 h / 0 - 20 °C 8: pyridine / 4 h / 60 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

38
[ 533-67-5 ]
[ 360580-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 75 percent / LiHMDS / tetrahydrofuran / 2 h / 0 °C
	Multi-step reaction with 6 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 75 percent / LiHMDS / tetrahydrofuran / 2 h / 0 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

39
[ 533-67-5 ]
(E)-(5S,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-5,6-bis-trimethylsilanyloxy-hept-2-en-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

40
[ 533-67-5 ]
{(2S,3S)-3-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-butyl]-oxiranyl}-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

41
[ 533-67-5 ]
(E)-(5S,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-5,6-bis-trimethylsilanyloxy-hept-2-enoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

42
[ 533-67-5 ]
[ 1054711-96-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C
	Multi-step reaction with 8 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

43
[ 533-67-5 ]
(2R,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((R)-1-hydroxy-propyl)-tetrahydro-furan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: 75 percent / H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C 9: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C
	Multi-step reaction with 9 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: 75 percent / H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C 9: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

44
[ 533-67-5 ]
[ 1053633-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: acetic acid; H₂O; tetrahydrofuran / 3 h / 0 - 20 °C
	Multi-step reaction with 8 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: acetic acid; H₂O; tetrahydrofuran / 3 h / 0 - 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

45
[ 533-67-5 ]
[ 1054650-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C
	Multi-step reaction with 6 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

46
[ 533-67-5 ]
[ 1054667-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 85 percent / tributyl phosphine / triethylamine / 4 h / 20 °C 7: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C
	Multi-step reaction with 7 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 85 percent / tributyl phosphine / triethylamine / 4 h / 20 °C 7: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

47
[ 533-67-5 ]
Acetic acid (R)-1-((2S,4R,5S)-4-acetoxy-5-vinyl-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C 9: pyridine / 4 h / 60 °C
	Multi-step reaction with 9 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C 9: pyridine / 4 h / 60 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

48
[ 533-67-5 ]
Acetic acid (2R,3S,5S)-5-((R)-1-acetoxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: 75 percent / H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C 9: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C 10: pyridine / 4 h / 60 °C
	Multi-step reaction with 10 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: 75 percent / H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C 9: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C 10: pyridine / 4 h / 60 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

49
[ 533-67-5 ]
Acetic acid (2R,3S,5R,6S)-5-acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-vinyl-tetrahydro-pyran-3-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: acetic acid; H₂O; tetrahydrofuran / 3 h / 0 - 20 °C 9: pyridine / 4 h / 60 °C
	Multi-step reaction with 9 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: acetic acid; H₂O; tetrahydrofuran / 3 h / 0 - 20 °C 9: pyridine / 4 h / 60 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

50
[ 533-67-5 ]
[ 360580-57-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C
	Multi-step reaction with 6 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

51
[ 533-67-5 ]
[ 360580-59-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: 75 percent / H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C
	Multi-step reaction with 8 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C 8: 75 percent / H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

52
[ 533-67-5 ]
[ 360580-58-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C
	Multi-step reaction with 7 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 90 percent / Dess-Martin Periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C 7: 55 percent / n-butyllithium / tetrahydrofuran; various solvent(s) / 6 h / 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

53
[ 533-67-5 ]
Acetic acid (2R,3S,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C 7: pyridine / 4 h / 60 °C
	Multi-step reaction with 7 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C 7: pyridine / 4 h / 60 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

54
[ 533-67-5 ]
[ 360580-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C
	Multi-step reaction with 5 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

55
[ 533-67-5 ]
Acetic acid (R)-1-((2S,4R,5S)-4-acetoxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 85 percent / tributyl phosphine / triethylamine / 4 h / 20 °C 7: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C 8: pyridine / 4 h / 60 °C
	Multi-step reaction with 8 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 85 percent / tributyl phosphine / triethylamine / 4 h / 20 °C 7: BF₃*Et₂O / diethyl ether / 1 h / 0 - 20 °C 8: pyridine / 4 h / 60 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

56
[ 533-67-5 ]
[ 360580-62-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 85 percent / tributyl phosphine / triethylamine / 0 - 20 °C
	Multi-step reaction with 6 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 85 percent / tributyl phosphine / triethylamine / 0 - 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

57
[ 533-67-5 ]
[ 360580-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: 73 percent / tBuOOH; D(-)diethyl tartrate; Ti(OiPr)4 / CH₂Cl₂ / 2 h / -20 °C 6: 85 percent / tributyl phosphine / triethylamine / 4 h / 20 °C
	Multi-step reaction with 6 steps 1: 92 percent / tetrahydrofuran / 90 °C 2: 72 percent / imidazole / dimethylformamide / 3 h / 20 °C 3: 75 percent / imidazole / dimethylaminopyridine / tetrahydrofuran / 4 h / Heating 4: 90 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / 0 °C 5: L(+)diethyl tartrate; Ti(OiPr)4; tBuOOH / CH₂Cl₂ / 2 h / -20 °C 6: 85 percent / tributyl phosphine / triethylamine / 4 h / 20 °C

Reference： [1]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]
[2]Narayan, Radha S.; Sivakumar, Meenakshi; Bouhlel, Ezzeddine; Borhan, Babak [Organic Letters, 2001, vol. 3, # 16, p. 2489 - 2492]

58
[ 533-67-5 ]
[ 213255-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1.1: HCl 2.1: NaH 3.1: m-CPBA; BF₃*Et₂O 4.1: LiAlH₄ 5.1: imidazole 6.1: Swern oxidation 7.1: LDA / tetrahydrofuran / -78 °C 7.2: tetrahydrofuran / 0.17 h / -78 °C 8.1: DIBAL-H 9.1: CSA 10.1: TBAF / tetrahydrofuran 11.1: 77 percent / NMO / TPAP

Reference： [1]Takahashi, Takashi; Hirose, Yoichiro; Iwamoto, Hajime; Doi, Takayuki [Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 5742 - 5743]

59
[ 533-67-5 ]
(S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionitrile N-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 13 steps 1.1: HCl 2.1: NaH 3.1: m-CPBA; BF₃Et₂O 4.1: LiAlH₄ 5.1: imidazole 6.1: Swern oxidation 7.1: LDA / tetrahydrofuran / -78 °C 7.2: tetrahydrofuran / 0.17 h / -78 °C 8.1: DIBAL-H 9.1: CSA 10.1: TBAF / tetrahydrofuran 11.1: 77 percent / NMO / TPAP 12.1: 73 percent / NH₂OHHCl; pyridine 13.1: NaOCl / H₂O / 0.25 h / 0 °C

Reference： [1]Takahashi, Takashi; Hirose, Yoichiro; Iwamoto, Hajime; Doi, Takayuki [Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 5742 - 5743]

60
[ 533-67-5 ]
[ 213255-14-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1.1: HCl 2.1: NaH 3.1: m-CPBA; BF₃Et₂O 4.1: LiAlH₄ 5.1: imidazole 6.1: Swern oxidation 7.1: LDA / tetrahydrofuran / -78 °C 7.2: tetrahydrofuran / 0.17 h / -78 °C 8.1: DIBAL-H 9.1: CSA 10.1: TBAF / tetrahydrofuran 11.1: 77 percent / NMO / TPAP 12.1: 73 percent / NH₂OHHCl; pyridine

Reference： [1]Takahashi, Takashi; Hirose, Yoichiro; Iwamoto, Hajime; Doi, Takayuki [Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 5742 - 5743]

61
[ 533-67-5 ]
(4aR,9S,9aS)-9-Benzyloxy-9a-benzyloxymethyl-2,2-dimethyl-5-methylene-hexahydro-cyclohepta[1,3]dioxin-7-one oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 14 steps 1.1: HCl 2.1: NaH 3.1: m-CPBA; BF₃Et₂O 4.1: LiAlH₄ 5.1: imidazole 6.1: Swern oxidation 7.1: LDA / tetrahydrofuran / -78 °C 7.2: tetrahydrofuran / 0.17 h / -78 °C 8.1: DIBAL-H 9.1: CSA 10.1: TBAF / tetrahydrofuran 11.1: 77 percent / NMO / TPAP 12.1: 73 percent / NH₂OHHCl; pyridine 13.1: NaOCl / H₂O / 0.25 h / 0 °C 14.1: triethylamine / 3 h / 20 °C

Reference： [1]Takahashi, Takashi; Hirose, Yoichiro; Iwamoto, Hajime; Doi, Takayuki [Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 5742 - 5743]

62
[ 533-67-5 ]
[ 87698-02-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaBH₄ / ethanol / 1 h / Ambient temperature 2: pyridine / benzene / Ambient temperature

Reference： [1]Tymiak,A.A.; Rinehart,K.L. [Journal of the American Chemical Society, 1983, vol. 105, p. 7396]

63
[ 50-89-5 ]
[ 533-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 70 percent / pH 10.6 / H₂O / 10 h / 0 °C / Irradiation 2: pH 10.5 / H₂O / 90 °C
	Multi-step reaction with 2 steps 1: 30 percent / pH 11.2 / H₂O / 6 h / 0 °C / Irradiation 2: H₂O / Heating
	With potassium dihydrogenphosphate; water at 55℃; for 1h;

Reference： [1]Saito,I.; Sugiyama,H.; Matsuura,T. [Journal of the American Chemical Society, 1983, vol. 105, p. 6989]
[2]Saito,I.; Sugiyama,H.; Matsuura,T. [Journal of the American Chemical Society, 1983, vol. 105, p. 6989]
[3]Rivero, Cintia W.; De Benedetti, Eliana C.; Sambeth, Jorge E.; Lozano, Mario E.; Trelles, Jorge A. [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 19, p. 6059 - 6062]

64
[ 533-67-5 ]
[ 5517-48-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 50percent aq. acetic acid / 0.17 h 2: hydrogen / palladium/barium sulfate / H₂O / 760 Torr / Ambient temperature

Reference： [1]Scensny, Patricia M.; Hirschhorn, Susan G.; Rasmussen, James R. [Carbohydrate Research, 1983, vol. 112, p. 307 - 312]

65
[ 533-67-5 ]
[ 2490-91-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 50percent aq. acetic acid / 0.17 h 2: hydrogen / palladium/barium sulfate / H₂O / 760 Torr / Ambient temperature

Reference： [1]Scensny, Patricia M.; Hirschhorn, Susan G.; Rasmussen, James R. [Carbohydrate Research, 1983, vol. 112, p. 307 - 312]

66
[ 533-67-5 ]
4-[(2S,3R)-3-(Toluene-4-sulfonyloxymethyl)-oxiranyl]-butyric acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 82 percent / benzoic acid / 1,2-dimethoxy-ethane / 5 h / Heating 2: 97 percent / H₂ / Pd-C / ethanol / 25 °C / 760 Torr 3: 75 percent / pyridine / 24 h / 0 °C 4: 96 percent / K₂CO₃ / methanol / 25 °C

Reference： [1]Corey, E. J.; Marfat, Anthony; Munroe, John; Kim, Kwan Soo; Hopkins, Paul B.; Brion, Francis [Tetrahedron Letters, 1981, vol. 22, p. 1077 - 1080]

67
[ 533-67-5 ]
[ 76745-17-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 82 percent / benzoic acid / 1,2-dimethoxy-ethane / 5 h / Heating 2: 97 percent / H₂ / Pd-C / ethanol / 25 °C / 760 Torr 3: 75 percent / pyridine / 24 h / 0 °C

Reference： [1]Corey, E. J.; Marfat, Anthony; Munroe, John; Kim, Kwan Soo; Hopkins, Paul B.; Brion, Francis [Tetrahedron Letters, 1981, vol. 22, p. 1077 - 1080]

68
[ 533-67-5 ]
[ 78606-80-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / benzoic acid / 1,2-dimethoxy-ethane / 5 h / Heating 2: 97 percent / H₂ / Pd-C / ethanol / 25 °C / 760 Torr

Reference： [1]Corey, E. J.; Marfat, Anthony; Munroe, John; Kim, Kwan Soo; Hopkins, Paul B.; Brion, Francis [Tetrahedron Letters, 1981, vol. 22, p. 1077 - 1080]

69
[ 533-67-5 ]
[ 78606-79-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 82 percent / benzoic acid / 1,2-dimethoxy-ethane / 5 h / Heating 2: 97 percent / H₂ / Pd-C / ethanol / 25 °C / 760 Torr 3: 75 percent / pyridine / 24 h / 0 °C 4: 96 percent / K₂CO₃ / methanol / 25 °C 5: 96 percent / pyridine / 1 h / 25 °C

Reference： [1]Corey, E. J.; Marfat, Anthony; Munroe, John; Kim, Kwan Soo; Hopkins, Paul B.; Brion, Francis [Tetrahedron Letters, 1981, vol. 22, p. 1077 - 1080]

70
[ 93857-40-0 ]
[ 533-67-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water Stage #2: With sodium hypochlorite; acetic acid In water at 40 - 45℃; for 2h;	5 Example 5; Production of D-2-deoxyribose After adjusting a 36.9 percent by weight aqueous solution (40 g) of sodium 3-deoxy-D-mannonate to pH 5 with hydrochloric acid, a 13 percent by weight aqueous solution (36.5 g) of sodium hypochlorite was added dropwise over 1 hour, while keeping the reaction temperature within a range from 40° C. to 45° C. and controlling pH within a range from 5 to 6 with acetic acid. After the completion of dropwise addition, the reaction mixture was aged for 1 hour and thereby yielded an aqueous solution (80.2 g) containing 9.3 g of target D-2-deoxyribose in a yield of 95% on the basis of 3-deoxy-D-mannonic acid. The oxidation-reduction potential in the reaction was 370 mV before the addition of sodium hypochlorite, was 960 to 1030 mV during the addition and dropped to 540 mV 30 minutes after the completion of the addition.
94%	Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water Stage #2: With hydrogenchloride; sodium hypochlorite; acetaldehyde In water at 40 - 45℃; for 2h;	8 Example 5; Production of D-2-deoxyribose After adjusting a 36.9 percent by weight aqueous solution (40 g) of sodium 3-deoxy-D-mannonate to pH 5 with hydrochloric acid, a 90 percent by weight aqueous solution (0.8 g) of acetaldehyde was added. Then, a 13 percent by weight aqueous solution (36.5 g) of sodium hypochlorite was added dropwise over 1 hour, while keeping the reaction temperature within a range from 40° C. to 45° C. and controlling pH within a range from 5 to 6 with hydrochloric acid. After the completion of dropwise addition, the reaction mixture was aged for 1 hour and thereby yielded an aqueous solution (82.8 g) containing 9.2 g of target D-2-deoxyribose in a yield of 94% on the basis of 3-deoxy-D-mannonic acid. The oxidation-reduction potential in the reaction was 370 mV before the addition of sodium hypochlorite, was 960 to 1030 mV during the addition and dropped to 530 mV 30 minutes after the completion of the addition.
94%	Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water Stage #2: With hydrogenchloride; sodium hypochlorite; formaldehyd In water at 40 - 45℃; for 2h;	7 Example 5; Production of D-2-deoxyribose After adjusting a 36.9 percent by weight aqueous solution (40 g) of sodium 3-deoxy-D-mannonate to pH 5 with hydrochloric acid, a 40% aqueous solution (1.3 g) of formaldehyde was added. Then, a 13 percent by weight aqueous solution (36.5 g) of sodium hypochlorite was added dropwise over 1 hour, while keeping the reaction temperature within a range from 40° C. to 45° C. and controlling pH within a range from 5 to 6 with hydrochloric acid. After the completion of dropwise addition, the reaction mixture was aged for 1 hour and thereby yielded an aqueous solution (83.3 g) containing 9.2 g of target D-2-deoxyribose in a yield of 94% on the basis of 3-deoxy-D-mannonic acid. The oxidation-reduction potential in the reaction was 370 mV before the addition of sodium hypochlorite, was 960 to 1030 mV during the addition and dropped to 530 mV 30 minutes after the completion of the addition.

94%	Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water Stage #2: With sodium hypochlorite; acetaldehyde; acetic acid In water at 40 - 45℃; for 2h;	9 Example 5; Production of D-2-deoxyribose After adjusting a 36.9 percent by weight aqueous solution (40 g) of sodium 3-deoxy-D-mannonate to pH 5 with hydrochloric acid, a 90% aqueous solution (0.8 g) of acetaldehyde was added. Then, a 13 percent by weight aqueous solution (36.5 g) of sodium hypochlorite was added dropwise over 1 hour, while keeping the reaction temperature in a range from 40° C. to 45° C. and controlling pH within a range from 5 to 6 with acetic acid. After the completion of dropwise addition, the reaction mixture was aged for 1 hour and thereby yielded an aqueous solution (81 g) containing 9.2 g of target D-2-deoxyribose in a yield of 94% on the basis of 3-deoxy-D-mannonic acid. The oxidation-reduction potential in the reaction was 370 mV before the addition of sodium hypochlorite, was 960 to 1030 mV during the addition and dropped to 550 mV 30 minutes after the completion of the addition.
93%	Stage #1: sodium 3-deoxy-D-mannonate With sodium hypochlorite In water for 1 - 4h; Stage #2: With sodium sulfite In water	1 Example 1; Production of D-2-deoxyribose with a reducing agent To a 25 percent by weight aqueous solution (44.7 g) of sodium 3-deoxy-D-mannonate under water-cooling was added dropwise a 8.9 percent by weight aqueous solution (60.2 g) of sodium hypochlorite over 1 hour, while controlling pH within a range from 4.5 to 5.0. Immediately after the completion of dropwise addition, sodium sulfite was added. In this procedure, it was checked using an aqueous solution of potassium iodide that hypochlorous acid was not detected. The reaction system was sequentially analyzed by high-performance liquid chromatography (HPLC), and the result is shown in Table 1. Table 1 shows that D-2-deoxyribose was produced in a reaction yield of 95% with substantially no excess reaction. [0070] Conditions for HPLC analyses of the material and product are as follows. [0071] Conditions for HPLC analysis of the material: [0072] Column: Shodex Asahipak NH2P-50 4E (from Showa Denko K. K.) [0073] Flow rate: 1 ml/min. [0074] Column temperature: 40° C. [0075] Detection wavelength: 210 nm [0076] Mobile phase: 50 mM NaH2PO4 aqueous solution Conditions for HPLC analysis of the product: [0077] Column: Shodex Sugar SC1011(from Showa Denko K. K.) [0078] Flow rate: 1 ml/min. [0079] Column temperature: 80° C. [0080] Detector: light scattering detector (detection sensitivity: 400 mV, Ti: 35° C., T2: 45° C., nitrogen pressure: 0.15 MPa) [0081] Mobile phase: H2O
93%	Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water Stage #2: With sodium hypochlorite; formic acid In water at 40 - 45℃; for 2h;	6 Example 5; Production of D-2-deoxyribose After adjusting a 36.9 percent by weight aqueous solution (40 g) of sodium 3-deoxy-D-mannonate to pH 5 with hydrochloric acid, a 13 percent by weight aqueous solution (59 g) of sodium hypochlorite was added dropwise over 1 hour, while keeping the reaction temperature within a range from 40° C. to 45° C. and controlling pH within a range from 5 to 6 with formic acid. After the completion of dropwise addition, the reaction mixture was aged for 1 hour and thereby yielded an aqueous solution (100.2 g) containing 9.1 g of target D-2-deoxyribose in a yield of 93% on the basis of 3-deoxy-D-mannonic acid. The oxidation-reduction potential in the reaction was 370 mV before the addition of sodium hypochlorite, was 960 to 1030 mV during the addition and dropped to 510 mV 30 minutes after the completion of the addition.

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - US2004/254368, 2004, A1 Location in patent: Page 5-6
[2]Current Patent Assignee: MITSUI CHEMICALS,INC. - US2004/254368, 2004, A1 Location in patent: Page 6
[3]Current Patent Assignee: MITSUI CHEMICALS,INC. - US2004/254368, 2004, A1 Location in patent: Page 6
[4]Current Patent Assignee: MITSUI CHEMICALS,INC. - US2004/254368, 2004, A1 Location in patent: Page 6
[5]Current Patent Assignee: MITSUI CHEMICALS,INC. - US2004/254368, 2004, A1 Location in patent: Page 4
[6]Current Patent Assignee: MITSUI CHEMICALS,INC. - US2004/254368, 2004, A1 Location in patent: Page 6

71
[ 1518-59-8 ]
[ 50480-80-3 ]
[ 533-67-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: D-<i>arabino</i>-3-deoxy-hexonic acid; 3-deoxy-D-arabino-hexono-1,4-lactone With sodium carbonate In water at 20℃; Stage #2: With sodium hypochlorite In water for 1 - 4h; Stage #3: With sodium sulfite In water	2 Example 2; Production of D-2-deoxyribose by hydrolysis of a lactone with a base and decarboxylation with a reducing agent To a 28 percent by weight (in terms of carboxylic acids) aqueous solution (13.0 g) of a 86:14 by mole mixture of 3-deoxy-D-mannonic acid and 3-deoxy-D-mannonolactone was added sodium carbonate at room temperature to pH 8.8 to thereby hydrolyze the lactone. A 8.9 percent by weight aqueous solution (21.3 g; 1.26 equivalent) of sodium hypochlorite was added dropwise to the reaction mixture over 1 hour under water-cooling while adjusting the pH within a range from 4.5 to 5.0 with concentrated hydrochloric acid. Immediately after the completion of dropwise addition, sodium sulfite was added. In this procedure, it was checked using an aqueous solution of potassium iodide that hypochlorous acid was not detected. The reaction system was sequentially analyzed by HPLC, and the result is shown in Table 2. [0084] Table 2 shows that D-2-deoxyribose was produced from a mixture with corresponding lactone in a reaction yield of 93% with substantially no excess reaction.

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - US2004/254368, 2004, A1 Location in patent: Page 4-5

72
[ 533-67-5 ]
[ 62-53-3 ]
[ 1279049-09-0 ]

Yield	Reaction Conditions	Operation in experiment
30%		11 From the generated product, inorganic salt was filtered out, followed by addition of 0.33 g of aniline to synthesize 2-deoxy-N-phenyl-D-rebosilamine for analysis (the total yield from KDG of 30%). The analysis values are shown below. 1H NMR (DMSO): 1.7 to 1.9 (2H, m), 3.4 to 3.7 (4H, m), 4.39 (1 H, d), 4.6 to 4.7 (2H, m), 6.38 (1H, d), 6.5 to 6.7 (3H, m), 7.0 to 7.1 (2H, m)

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - EP1589021, 2005, A1 Location in patent: Page/Page column 11

73
potassium 2-dehydro-3-deoxy-D-gluconate [ No CAS ]
[ 533-67-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: potassium 2-dehydro-3-deoxy-D-gluconate With sulfuric acid; hydrogen In water at 50℃; Stage #2: With calcium carbonate In water Stage #3: With calcium hydroxide; carbon dioxide; dihydrogen peroxide; copper diacetate; iron(II) sulfate more than 3 stages;	11 Synthesis of D-2-deoxyribose Example 11Synthesis of D-2-deoxyribose 0.6 g of sulfuric acid and 0.1 g of 10% palladium carbon (48% water-containing product) were added to an aqueous solution containing KDG potassium salt (5.73 mmole), and the resulting mixture was heated to 50°C and reacted under a hydrogen flow. After the reaction was completed, palladium carbon was filtered out, and 0.67 g of calcium carbonate was added thereto. A precipitate was filtered out and 0.42 g of calcium hydroxide was added to the filtrate. Furthermore, carbonic gas was blown thereinto and heated to 100°C. Then, the precipitate was filtered out. A mixture of 1 ml of water, 9.6 mg of iron (II) sulfate heptahydrate and 8.8 g of barium acetate which was prepared in advance was added to the filtrate. The resulting solution was heated to 50°C. Further, 0.4 g of 30% hydrogen peroxide water was added three times at an interval of 30 minutes. After the reaction was completed, as a result of the HPLC analysis, D-2-deoxyribose was obtained with the reaction yield of 47%.

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - EP1589021, 2005, A1 Location in patent: Page/Page column 11

74
[ 17510-99-5 ]
[ 533-67-5 ]

Yield	Reaction Conditions	Operation in experiment
51%	With cerium(IV) sulphate; sulfuric acid In water at 37℃;	10 Synthesis of D-2-deoxyribose Example 10 Synthesis of D-2-deoxyribose Palladium carbon contained in the reaction solution obtained in Example 1 was filtered out from the reaction solution. Then 1.8 g of cerium (IV) sulfate tetrahydrate and 0.87 g of sulfuric acid were added to 20 ml of water at 37°C and the resulting mixture was dropped. After the reaction was completed, the reaction solution was analyzed according to HPLC. As a result, the total yield from KDG was 51%.

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - EP1589021, 2005, A1 Location in patent: Page/Page column 11

75
[ 582-33-2 ]
sodium boron cyanohydride [ No CAS ]
[ 533-67-5 ]
[ 334792-30-2 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In methanol; dichloromethane; chloroform	S.10 Intermediate 10-1: Ethyl 3-{(3S,4R)-3,4,5-(trihydroxy) pentan-1-ylamino}benzoate Intermediate 10-1: Ethyl 3-{(3S,4R)-3,4,5-(trihydroxy) pentan-1-ylamino}benzoate Methanol (50 ml) was added to 1.34 g of 2-deoxy-D-ribose to prepare a solution. Separately, 50 ml of methylene chloride was added to 1.60 g of ethyl 3-aminobenzoate to prepare a solution which was then added to the above methanol solution. A reaction was allowed to proceed at room temperature for 16 hr. Acetic acid (1.0 ml) and 500 mg of sodium boron cyanohydride were then added thereto in that order, and a reaction was allowed to proceed at room temperature for 4 hr. The reaction solution was concentrated under the reduced pressure, and the residue was extracted with 300 ml of chloroform. The organic layer was washed with 200 ml of a saturated aqueous sodium hydrogencarbonate solution containing aminor amount of sodium chloride. The aqueous layer was subjected to back extraction with 100 ml of chloroform. The chloroform layers were combined and were then dried over anhydrous sodium sulfate, followed by concentration under the reduced pressure. The residue was purified by column chromatography on silica gel (100 g, chloroform:methanol:concentrated aqueous ammonia=10:1:0.1→10:1.3:0.1) to give 2.23 g of the title compound.
	With acetic acid In methanol; dichloromethane; chloroform	9 Intermediate 14: Ethyl 3-{(3S,4R)-3,4,5-(trihydroxy)pentan-1-ylamino}benzoate Intermediate 14: Ethyl 3-{(3S,4R)-3,4,5-(trihydroxy)pentan-1-ylamino}benzoate Methanol (50 ml) was added to 1.34 g of 2-deoxy-D-ribose to prepare a solution. Separately, 50 ml of methylene chloride was added to 1.60 g of ethyl 3-aminobenzoate to prepare a solution which was then added to the above methanol solution. A reaction was allowed to proceed at room temperature for 16 hr. Acetic acid (1.0 ml) and 500 mg of sodium boron cyanohydride were then added thereto in that order, and a reaction was allowed to proceed at room temperature for 4 hr. The reaction solution was concentrated under the reduced pressure, and the residue was extracted with 300 ml of chloroform. The organic layer was washed with 200 ml of a saturated aqueous sodium hydrogencarbonate solution containing a minor amount of sodium chloride. The aqueous layer was subjected to back extraction with 100ml of chloroform. The chloroform layers were combined and were then dried over anhydrous sodium sulfate, followed by concentration under the reduced pressure. The residue was purified by column chromatography on silica gel (100 g, chloroform-methanol-concentrated aqueous ammonia = 10: 1: 0.1 → 10: 1.3: 0.1) to give 2.23 g of the title compound. Physicochemical properties of intermediate 14

Reference： [1]Current Patent Assignee: MEIJI HOLDINGS CO., LTD - US2003/40531, 2003, A1
[2]Current Patent Assignee: MEIJI HOLDINGS CO., LTD - EP1229024, 2002, A1

76
[ 533-67-5 ]
[ 100-39-0 ]
[ 170984-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; tetra-(n-butyl)ammonium iodide In tetrahydrofuran; methanol; dichloromethane	A Preparation of Methyl 3,5-di-O-benzyl-2-deoxy-D-erythropentoside Example A Preparation of Methyl 3,5-di-O-benzyl-2-deoxy-D-erythropentoside To a solution of 2-deoxy-D-ribose (50 g, 373 mmol) in dry methanol (900 ml) was added a 1% solution of dry hydrogen chloride in methanol (100 ml). The mixture was kept in a stoppered flask for 30 minutes after which the reaction was stopped by adding, with vigorous stirring, silver carbonate (10 g). The mixture was filtered by gravity and the colourless filtrate evaporated to a syrup using a dry rotary evaporator. Residual methanol was then removed by repeated evaporation with dry THF. The syrup was then dissolved in dry THF (470 ml). Under an atmosphere of dry nitrogen, at 0° C., with stirring sodium hydride in a 50% oil-dispersion (39.4 g, 821 mmol) was slowly added to the THF mixture. Next, dry tetrabutylammonium iodide (30.3 g, 82.1 mmol) was added followed by benzyl bromide (140 g, 821 mmol), which was added over 1 hour. After stirring for 60 hours at room temperature, with exclusion of moisture, TLC (hexane-ethyl acetate [4:1]) showed almost complete conversion to two faster moving components (Rf 0.47 and 0.36). The THF was removed in vacuo, the residue dissolved in dichloromethane and then poured into ice/water. The dichloromethane solution was extracted from this mixture and then dried over magnesium sulphate. The dichloromethane was evaporated under reduced pressure and the resulting residue applied to a silica gel column eluted with hexane-ethyl acetate (4:1). Combination of the appropriate fractions gave the α (Rf0.36) and β (Rf 0.47) isomers of the title product as a clear, colourless syrup NMR SPECTRA α-isomer (1 H) δ (d6 DMSO):7.56-7.17 (10H,d,aromatic), 5.12-5.00 (1H,q;H-1), 4.60-4.45 (4H,m, PhCH2 O), 4.40-3.86 (2H,m,H-3, H-4), 3.58-3.42 (2H,d,H-5), 3.40 (3H,s,CH3),2.40-1.80 (2H,m,H-2). (13 C) δ (CDCl3): 128.3-127.6 aromatic), 105.2 (C-1), 82.1 (C-3 or C-4), 78.6 (C-3 or C-4), 73.4 (PhCH2 O), 71.5 (PhCH2 O), 70.2 (C-5), 55.1 (OMe), 38.9 (C-2). β- isomer (1 H) δ (d6 DMSO):7.50-7.20 (10H,d,aromatic), 5.18-5.02 (1H,q,H-1), 4.65-4.43, (4H,d, PhCH2 O), 4.43-4.00 (2H,m,H- 3,H-4), 3.60-3.42 (2H,m,H-5), 3.30 (3H,s,CH3), 2.45-2.05 (2H,m,H-2). (13 C) δ (CDCl3): 128.3-127.6 (aromatic), 105.4 (C-1), 82.8 (C-3 or C-4), 80.0 (C-3 or C-4), 73.3 (PhCH2 O), 72.0 (PhCH2 O), 70.2 (C-5), 54.9 (OMe), 39.3 (C-2).

Reference： [1]Current Patent Assignee: UNIVERSITY OF BIRMINGHAM; UNIVERSITY OF VERMONT - US5356882, 1994, A

77
methanolic hydrogen chloride [ No CAS ]
[ 533-67-5 ]
[ 76-83-5 ]
methy 2-deoxy-5-trityl-D-ribofuranoside [ No CAS ]
[ 105454-46-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	In pyridine	1 Preparation of Methyl 2-Deoxy-5-trityl-D-ribofuranoside EXAMPLE 1 Preparation of Methyl 2-Deoxy-5-trityl-D-ribofuranoside About 25 g of 2-deoxy-D-ribose were placed in a dried 2000 ml round-bottomed flask under a stream of N2. The flask was cooled, and 873 ml of 0.05% methanolic hydrogen chloride added with stirring. After 15 minutes, during which time the sugar had dissolved, about 5 g of silver carbonate were added, and the resulting reaction mixture stirred vigorously for 0.5 hours. The reaction mixture was filtered thru hyflosupercel and the filter cake washed thoroughly with methanol. Evaporation of the methanol from the filtrate left, as a residue, about 27.5 g (100% yield) of a mixture of α and β-methyl 2-deoxy-D-ribofuranoside. This compound was dissolved in 558 ml of pyridine. 76.93 g of tritylchloride were added under N2, and the reaction mixture was stirred at room temperature for about 72 hours at which time TLC (SiO2; 3:1 cyclohexane/ethyl acetate) showed that the reaction had gone to completion. The pyridine was removed by evaporation under reduced pressure, and the residue, comprising methy 2-deoxy-5-trityl-D-ribofuranoside formed in the above reaction, was dissolved in a mixture of chloroform and water. The chloroform layer was separated, and the aqueous layer extracted with chloroform. The chloroform extracts were combined; the combined extracts were washed with brine and then dried. Evaporation of the solvent yielded a residue which was purified by preparative HPLC. 65.4 g (90% yield) of methyl 2-deoxy-5-trityl-D-ribofuranoside were thus obtained.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US4675390, 1987, A

78
[ 533-67-5 ]
[ 1885-14-9 ]
[ 100-46-9 ]
[ 64774-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium cyanoborohydride In 1,4-dioxane; water	1.A 3-Benzyl-6(S)-dihydroxymethyltetrahydro-1,3-oxazin-2-one (A) A solution of benzylamine (2.14 g, 0.02 moles) in water (25 ml) was adjusted to pH5 with 5N hydrochloric acid. 2-Deoxy-D-ribose (1.34 g, 0.01 mole) and sodium cyanoborohydride (0.062 g, 0.01 mole) were added and the solution was allowed to stand for 15 hours at room temperature. The pH of the solution was adjusted to 10 with sodium carbonate and the mixture was washed several times with ethyl acetate. The aqueous solution was cooled to 0° C, and phenyl chloroformate (1.7 g., 0.011 mmoles) in dioxan (15 ml) was added with stirring. After 3 hours at 0° C., the reaction was allowed to warm to room temperature, the pH was adjusted to 7 by the addition of 5N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic extract was dried over magnesium sulphate and evaporated under reduced pressure to yield 1,2(S),3(S)-trihydroxy-5-[N-phenoxycarbonyl-N-benzylamino]pentane (2.1 g.) as an oil which slowly solidified on standing. δ (CDCl3 + D2 O) 7.2 (10 H, m); 4,5 (2H, s); 3,5 (6 H,m) 1.8 (2H,m). νmax. (film) 3400, 1705, 1600 cm-1.

Reference： [1]Current Patent Assignee: PFIZER INC - US4107435, 1978, A

79
[ 533-67-5 ]
[ 100-46-9 ]
[ 64774-54-5 ]

Yield	Reaction Conditions	Operation in experiment
59.5%	In methanol; water	3.A 3-Benzyl-6(S)-dihydroxymethyltetrahydro-1,3-oxazin-2-one (A) 2-Deoxy-D-ribose (100 g; 0.746 mole) and benzylamine (96 g; 0.897 mole) were dissolved in methanol (400 ml) and water (40 ml) and hydrogenated at 50° C and 50 p.s.i. in the presence of platinum oxide catalyst (4.0 g) until hydrogen uptake was complete. The catalyst was filtered off and the filtrate was cooled in an ice bath. The resulting crystalline precipitate was collected, washed with cold methanol, and dried to give 5-(benzylamino)-1,2(S),3(S)-trihydroxypentane (100 g; 59.5% yield). A sample was recrystallized from ethyl acetate, m.p. 117°-118.5° C, δ (DMSO-D6) 7.3 (5H, s); 3.9 (3H, m, exchangeable with D2 O); 3.7 (2H, s); 3.4 (4H, m); 2.6 (2H, m); 1.6 (2H, m). νmax. 3370, 3310, 3290 cm-1. (Found: C, 64.3; H, 8.5; N, 6.1. C12 H19 NO3 requires: C, 64.0; H, 8.5; N, 6.2%).

Reference： [1]Current Patent Assignee: PFIZER INC - US4107435, 1978, A

80
[ 533-67-5 ]
[ 100-46-9 ]
5-amino-1,2(S),3(S)-trihydroxy-pentane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%.	With sodium cyanoborohydride In methanol; water	7.A 6-(S)-Dihydroxymethyltetrahydro-1,3-oxazin-2-one (A) A solution of benzylamine (4.8 g., 48 mmole) in water (40 ml.) was acidified to pH 5 with 5N hydrochloric acid. 2-Deoxy-D-ribose (3.0 g., 27.5 mmole) and sodium cyanoborohydride (1.35 g., 21.5 mmole) were added and the solution was stirred and allowed to stand overnight at room temperature. The solution was basified to pH 10 with sodium hydroxide, washed several times with ethyl acetate to remove excess benzylamine, and acidified to pH 4 with hydrochloric acid. Methanol (60 ml.) was added and the crude mixture was hydrogenated at 50° C. and 50 p.s.i. in the presence of 10% palladium-on-charcoal catalyst, fresh catalyst being added after 24 hours. After a further 4 days, the solution was filtered and evaporated, the product being chromatographed on Amberlite CG 50 ion exchange resin (NH4+ form) eluding with 0.1N ammonium hydroxide to give 5-amino-1,2(S),3(S)-trihydroxy-pentane (1.6 g., 53%. m/e

Reference： [1]Current Patent Assignee: PFIZER INC - US4107435, 1978, A

81
[ 533-67-5 ]
[ 874-60-2 ]
[ 75-36-5 ]
[5-chloro-3-[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In pyridine; methanol	1.a 5-chloro-2-(4-methyl-benzoyloxymethyl)-3-(4-methyl-benzoyloxy)-tetrahydro-furan 5-chloro-2-(4-methyl-benzoyloxymethyl)-3-(4-methyl-benzoyloxy)-tetrahydro-furan 45.0 g (335.5 mmol) of 2-deoxy-D-ribose (Fluka 31170) were dissolved in 540 ml of anhydrous methanol. To this solution a mixture of 90 ml methanol and 1.53 ml (21.5 mmol) acetyl chloride (Aldrich 40,279-6) were added drop wise at room temperature. The resulting mixture was stirred for an additional 15 min. at room temperature. After the addition of 18.0 g (214.3 mmol) sodium bicarbonate the resulting suspension was stirred for 15 min. After filtration of the suspension the solvent was removed by distillation. To the oily brown residue 75 ml of anhydrous pyridine were added and subsequently the solvent was removed in a vacuum on a rotary evaporator. This procedure was repeated three times. The remaining residue was dissolved in 270 ml anhydrous pyridine and cooled to 0° C. At this temperature 99 ml (748.6 mmol) of p-toluoyl chloride (Aldrich 10,663-1) were added drop wise over a period of 90 minutes. Afterwards the reaction mixture was stirred for an additional 12 hours at room temperature. The suspension was poured on 1.5 l sludge and the aqueous phase was extracted three times each with 600 ml dichloromethane.
	With sodium hydrogencarbonate In pyridine; methanol	1.a.b Preparation of indole nucleoside b) 5-chloro-2-(4-methyl-benzoyloxymethyl)-3-(4-methyl-benzoyloxy)-tetrahydrofuran 45.0 g (335.5 mmol) of 2-deoxy-D-ribose (Fluka 31170) were dissolved in 540 ml of anhydrous methanol. To this solution a mixture of 90 ml methanol and 1.53 ml (21.5 mmol) acetyl chloride (Aldrich 40,279-6) were added drop wise at room temperature. The resulting mixture was stirred for an additional 15 min. at room temperature. After the addition of 18.0 g (214.3 mmol) sodium bicarbonate the resulting suspension was stirred for 15 min. After filtration of the suspension the solvent was removed by distillation. To the oily brown residue 75 ml of anhydrous pyridine were added and subsequently the solvent was removed in a vacuum on a rotary evaporator. This procedure was repeated three times. The remaining residue was dissolved in 270 ml anhydrous pyridine and cooled to 0°C. At this temperature 99 ml (748.6 mmol) of p-toluoyl chloride (Aldrich 10,663-1) were added drop wise over a period of 90 minutes. Afterwards the reaction mixture was stirred for an additional 12 hours at room temperature. The suspension was poured on 1.5 l sludge and the aqueous phase was extracted three times each with 600 ml dichloromethane.
	With sodium hydrogencarbonate In pyridine; methanol	1.a.b Preparation of 5-Nitroindole nucleoside b) 5-chloro-2-(4-methyl-benzoyloxymethyl)-3-(4-methyl-benzoyloxy)-tetrahydrofuran 45.0 g (335.5 mmol) of 2-deoxy-D-ribose (Fluka 31170) were dissolved in 540 ml of anhydrous methanol (Ident. 0577286-001). To this solution a mixture of 90 ml methanol and 1.53 ml (21.5 mmol) acetyl chloride (Aldrich 40,279-6) were added drop wise at room temperature. The resulting mixture was stirred for an additional 15 min. at room temperature. After the addition of 18.0 g (214.3 mmol) sodium bicarbonate (Ident. 11270834-001) the resulting suspension was stirred for 15 min. After filtration of the suspension the solvent was removed by distillation. To the oily brown residue 75 ml of anhydrous pyridine were added and subsequently the solvent was removed in a vacuum on a rotary evaporator. This procedure was repeated three times. The remaining residue was dissolved in 270 ml anhydrous pyridine and cooled to 0°C. At this temperature 99 ml (748.6 mmol) of p-toluoyl chloride (Aldrich 10,663-1) were added drop wise over a period of 90 minutes. Afterwards the reaction mixture was stirred for an additional 12 hours at room temperature. The suspension was poured on 1.51 sludge and the aqueous phase was extracted three times each with 600 ml dichloromethane (Ident. 11270834-001).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2007/196852, 2007, A1
[2]Current Patent Assignee: ROCHE HOLDING AG - EP1842923, 2007, A1
[3]Current Patent Assignee: ROCHE HOLDING AG - EP1700922, 2006, A2

82
[ 67-56-1 ]
[ 533-67-5 ]
[ 874-60-2 ]
1-O-methyl-3,5-di-O-(p-toluoyl)-2-deoxy-D-ribofuranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methanol; 2-Deoxy-D-ribose With hydrogenchloride for 0.25h; Stage #2: With silver carbonate In methanol Stage #3: 4-methyl-benzoyl chloride In pyridine at 3 - 20℃;	9 [0068] 2-Deoxy-3,5-di-O-p-toluoyl)-?-D-ribofuranosyl chloride [0069] 2-Deoxy-D-ribose (24.2 g, 0.2 mol) was dissolved in anhydrous methanol (486 mL). 1% Methanolic HCl (54 mL, prepared by bubbling anhydrous HCl in methanol) was added and the vessel was sealed and was allowed to stand sealed for 15 minutes to form the methyl glycoside. Silver carbonate (10.0 g) was added. The mixture was shaken well and then filtered. The filtrate was concentrated in vacuo (aspirator, 30 C.) to an oil. Dry pyridine was added (2?10 mL) and the solution was concentrated in vacuo and then placed under high vacuum 30 C./0.3 mmHg for 1 h to give crude methyl glycoside (ca. 36 g). The glycoside was dissolved in dry pyridine (160 mL) and the solution was cooled to 3-5 C. (ice-water bath). p-Toluoyl chloride (68 g, 0.44 mol) was added dropwise while maintaining the temperature below 20 C. After the addition was complete, the mixture was allowed to stand at room temperature overnight. The next day, ice-cold water (600 mL) was added and the mixture was extracted with ether (2?400 mL) The combined ether extracts were washed successively with water (2?200 mL), dilute sulfuric acid (2.5 N, 2?300 mL), saturated sodium bicarbonate solution (2?400 mL), and dried (MgSO4). The mixture was filtered and the filtrate was concentrated at 30 C. in vacuo (aspirator, then 0.3 mm Hg for 1 h) to give 1-O-methyl-3,5-di-O-(p-toluoyl)-2-deoxy-D-ribofuranoside as a yellow syrup (ca. 90 g). The syrup was dissolved in glacial acetic acid (60 mL) and then added to acetic acid saturated with HCl gas (160 mL). While maintaining the temperature at 10 C., anhydrous HCl was passed into the solution for 10 minutes (the solution turned to a thick crystalline paste). The mixture was diluted with anhydrous ether (100 mL), filtered, and the resulting solid was recrystallized from toluene (500 mL) and dried in a vacuum desiccator over soda lime and P2O5 to give pure product, 44.0 g (51%), mp 117-119 C.

Reference： [1]Current Patent Assignee: TALMER BANK AND TRUST - US2004/39190, 2004, A1 Location in patent: Page 7

83
[ 109-80-8 ]
[ 533-67-5 ]
[ 50907-65-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogenchloride; water In chloroform at 20℃;
75%	With hydrogenchloride In chloroform; water at 0 - 20℃; Inert atmosphere;	(2R,3S)-4-(1,3-Dithian-2-yl)butane-1,2,3-triol (7) 2-Deoxy-D-ribose (6)(1.0 g, 7.46 mmol) was taken up in chloroform (3.5 mL) and aqueous hydrochloric acid (6 M; 5 mL) and the solution was cooled to 0 °C. 1,3-Propanedithiol (1.65 mL, 16.4 mmol) was added and the reaction was stirred at room temperature overnight. The precipitated product was collected by suction filtration and the filtrate was extracted with hot chloroform (75 mL). The product which crystallised from the extract was collected and combined with the remainder and dried over P2O5 to give the title compound (1.25 g, 75%) as a colourless solid. (Note: if aged 2-deoxy--ribose is used, the title compound can be dissolved in methanol and any brown impurities removed by filtration.) δH (500 MHz; CD3OD): 4.28 (1 H, dd, J 11.0, 3.5), 3.82 (1 H, ddd, J 10.0, 6.5, 2.0), 3.71 (1 H, dd, J 11.5, 4.0), 3.56 (1 H, dd, J 11.0, 6.5), 3.43 (1 H, ddd, J 6.5, 6.5, 4.0), 2.98-2.79 (4 H, m), 2.14-2.07 (2 H, m), 1.88-1.79 (1 H, m), 1.75 (1 H, ddd, J 14.0, 10.0, 3.5); δC (125 MHz; CD3OD): 76.4 (CH), 69.8 (CH), 64.6 (CH2), 44.8 (CH), 40.3 (CH2), 31.1 (CH2), 30.5 (CH2), 27.3 (CH2); []26 -37.0 (c 1.08, CH3OH), lit.[3] -33.2 (c 1.06, CH3OH); mp: 122-123 °C (lit.[4] 124-125 °C).

Reference： [1]Location in patent: scheme or table Morita, Masayuki; Haketa, Tasuku; Koshino, Hiroyuki; Nakata, Tadashi [Organic Letters, 2008, vol. 10, # 9, p. 1679 - 1682]
[2]Law, Katherine R.; McErlean, Christopher S.P. [Tetrahedron Letters, 2016, vol. 57, # 29, p. 3113 - 3116]

84
[ 533-67-5 ]
[ 1779-49-3 ]
[ 79364-36-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-Deoxy-D-ribose In tetrahydrofuran at 0 - 40℃; for 24h;
75%	Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-Deoxy-D-ribose In tetrahydrofuran at 35℃; for 24h;

Reference： [1]Urosa, Aitor; Marcos, Isidro S.; Díez, David; Padrón, José M.; Basabe, Pilar [Journal of Organic Chemistry, 2015, vol. 80, # 12, p. 6447 - 6455]
[2]Morita, Masayuki; Haketa, Tasuku; Koshino, Hiroyuki; Nakata, Tadashi [Organic Letters, 2008, vol. 10, # 9, p. 1679 - 1682]

85
[ 2226-96-2 ]
[ 533-67-5 ]
[ 1110727-11-1 ]

Yield	Reaction Conditions	Operation in experiment
38%	With dihydrogen peroxide; copper(l) chloride In water; acetic acid at 30℃; for 16h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

86
[ 67-56-1 ]
[ 533-67-5 ]
[ 51255-18-6 ]
[ 51255-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With acetyl chloride at 20℃;
20 % de	With hydrogenchloride In diethyl ether at 20℃; for 3h;

Reference： [1]Location in patent: experimental part Dangerfield, Emma Marie; Plunkett, Catherine Heather; Stocker, Bridget Louise; Timmer, Mattie Simon Maria [Molecules, 2009, vol. 14, # 12, p. 5298 - 5307]
[2]Shiozaki, Yoko; Sakurai, Shunya; Sakamoto, Ryu; Matsumoto, Akira; Maruoka, Keiji [Chemistry - An Asian Journal, 2020, vol. 15, # 5, p. 573 - 576]

87
[ 533-67-5 ]
[ 108-98-5 ]
[ 183075-04-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sulfuric acid In N,N-dimethyl-formamide

Reference： [1]Location in patent: scheme or table Haraguchi, Kazuhiro; Konno, Kiju; Yamada, Kaori; Kitagawa, Yasuyuki; Nakamura, Kazuo T.; Tanaka, Hiromichi [Tetrahedron, 2010, vol. 66, # 25, p. 4587 - 4600]

88
[ 533-67-5 ]
[ 34371-14-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With bromine; In water; at 20℃; for 120.0h;	Example 1A (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one A 500 mL round-bottomed flask was charged with 2-deoxy-D-ribose (10 g, 74.6 mmol) and water (60 mL), followed by the dropwise addition of bromine (59.6 g, 373 mmol). The contents were then stirred at room temperature for 5 days. The reaction mixture was then diluted with water (300 mL) and then extracted with tert-butyl methyl ether (3*200 mL). The aqueous layer was then neutralized with the addition of silver carbonate until the pH of the aqueous solution reached 6. The resulting solids were removed by filtration and the filtrate was concentrated under vacuum to provide a residue which was dissolved in ethyl acetate (200 mL), followed by the addition of magnesium sulfate. After sitting overnight, the solids were filtered off and the filtrate was concentrated to provide the title compound as an oil (7.72 g, 78%). 1H NMR (400 MHz, CDCl3) delta 1.83 (t, J=5.9 Hz, 1H), 2.13 (d, J=4.3 Hz, 1H), 2.57 (dd, J=18.1, 4.0 Hz, 1H), 3.00 (dd, J=18.0, 7.2 Hz, 1H), 3.85 (m, 1H), 3.97 (m, 1H), 4.46 (q, J=3.2 Hz, 1H), 4.65 (m, 1H).
	With bromine; In water; at 20℃; for 120.0h;Sealed tube;	EXAMPLE 3[0153] 2-deoxy-3,5-di-0-(?-butyldimethylsilyl)-D-ribonolactone (7).; To a solution of 2- deoxy-D-ribose (1.0 g, 7.45 mmol) in 6 mL of water was added Br2 (2 mL). The flask was sealed and the content was stirred at room temperature for 5 days. The resulting mixture was neutralized by adding silver carbonate until the pH was 7. The mixture was filtered and the filtrate was concentrated under reduced pressure to yield 2-deoxyribonolactone as a yellow oil. Without further purification, the crude product was dissolved in 20 mL of anhydrous DMF, and imidazole (2.53 g, 37.3 mmol) and t-butyldimethylsilyl chloride (4.5 g, 29.8 mmol) were added. The resulting solution was stirred at room temperature for 24 h, and quenched by addition of water. Water layer was extracted by ethyl acetate (3x10 mL), organic layers were combined, washed with brine and dried over anhydrous Na2SO4. Crude product was concentrated in vacuo. Flash chromatography (hexanes:ethyl acetate 20:1) afforded 7 (3.2 g, 8.9 mmol, 89% yield after two steps) as white solid, mp = 72-73 0C. 1H NMR (CDCl3, 400 MHz), delta ppm: 0.038 (s, 3H), 0.051 (s, 3H), 0.062 (s, 6H), 0.085 (s, 18H)5 2.36 (dd, J= 2.6, 17.7 Hz, IH), 2.79 (dd, J= 6.7, 17.7 Hz, IH), 3.73 (dd, J= 2.5, 11.5 Hz, IH), 3.78 (dd, J= 3.4, 11.5 Hz, IH), 4.30 (dd, J= 2.5, 5.2 Hz, IH), 4.48 (dt, J= 2.3, 6.6 Hz, IH). 13C NMR (125 MHz, CDCl3), delta ppm: -5.7, -5.5, -4.9, -4.8, 17.9, 18.2, 25.7, 25.8, 39.0, 62.5, 69.6, 88.1, 175.8. HRMS (ESI): calcd. for CnH36O4Si2: 360.2152; Found: 360.2155.
	With bromine; In water; at 20℃; for 120.0h;Sealed tube;	To a solution of 2-deoxy-D-ribose (150 mmol) in water (120 mL) was added bromine (40 mL) at room temperature. The vial was sealed. The reaction mixture was stirred at room temperature for 5 days, quenched with silver carbonate till pH= 7, filtered to remove salts, concentrated under reduced pressure and dried to afford crude compound, directly used in the next step without purification. The reaction was monitored by TLC.

Reference： [1]European Journal of Organic Chemistry,2013,p. 1306 - 1317
[2]Patent: US2017/57981,2017,A1 .Location in patent: Paragraph 0268; 0269; 0320; 0321
[3]RSC Advances,2014,vol. 4,p. 11023 - 11028
[4]Patent: WO2011/3018,2011,A2 .Location in patent: Page/Page column 40-41
[5]Patent: WO2015/81297,2015,A1 .Location in patent: Paragraph 00291

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	533-67-5	MDL No. :	MFCD00135904
Formula :	C₅H₁₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ASJSAQIRZKANQN-CRCLSJGQSA-N
M.W :	134.13	Pubchem ID :	5460005
Synonyms :	Deoxyribose;2-Deoxy-D-arabinose;(3S,4R)-3,4,5-Trihydroxypentanal;2-Deoxy-D-ribose	Chemical Name :	(3S,4R)-3,4,5-Trihydroxypentanal

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	29.83
TPSA :	77.76 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.72 cm/s

Log Po/w (iLOGP) :	0.66
Log Po/w (XLOGP3) :	-2.26
Log Po/w (WLOGP) :	-1.71
Log Po/w (MLOGP) :	-1.65
Log Po/w (SILICOS-IT) :	-0.63
Consensus Log Po/w :	-1.12

[ CAS No. 533-67-5 ] {[proInfo.proName]}

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[ 533-67-5 ] Synthesis Path-Upstream 1~1

[ 533-67-5 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

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Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	1.02
Solubility :	1390.0 mg/ml ; 10.4 mol/l
Class :	Highly soluble
Log S (Ali) :	1.16
Solubility :	1940.0 mg/ml ; 14.5 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	1.02
Solubility :	1410.0 mg/ml ; 10.5 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.36

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
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