7643-75-6|(2S,4S)-Pentane-1,2,3,4,5-pentaol| Ambeed

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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1
[ 5328-37-0 ]
[ 7643-75-6 ]

Yield	Reaction Conditions	Operation in experiment
	With platinum(IV) oxide; water Hydrogenation;
	With water; nickel Hydrogenation;
	With sodium hydroxide; nickel Hydrogenation;

	With nickel; cyclohexanol at 125℃; Hydrogenation;
	With sodium borate; water
	With sodium amalgam die Loesung muss durch verd.Schwefelsaeure stets neutral gehalten werden;
	With sodium tetrahydroborate
	With monospecific xylose reductase from yeast Candida intermedia; NADPH In phosphate buffer at 25℃;
	With potassium phosphate; recombinant rat brain aldo-keto reductase R₁B₁₀; NADP In methanol Enzymatic reaction;
	With sodium tetrahydroborate; sodium carbonate In water; dimethyl sulfoxide at 4 - 40℃;	2.7. Determination of sugars by GC-MS analysis General procedure: To determine the sugars in the glycosylated MAAs, the sugars were released by acid hydrolysis. Following a reduction to alditol, the acetylated derivatives were identified by GC-MS analysis [41]. The purified glycosylated MAA (approximately 20 μg) was hydrolyzedby 5% H2SO4 aq. (100 μL) at 75 °C for 8 h. After hydrolysis the pH was adjusted to 11 with solid Na2CO3. Sodium borohydrate solution (0.5 M in DMSO, 1 ml) was added and kept at 40 °C for 90 min and then incubated at 4 °C overnight to complete reduction. Glacial acetic acid (99.9%, 100 μl), 1-methylimidazole (200 μl) and acetic anhydride (1 ml) were added in this order at room temperature and kept at 40 °C for 10 min. After acetylation we added wate r(2.5 ml) and the acetylated derivatives were extracted by CH2Cl2 (1 ml). An organic phase (lower layer) was recovered and dried with Na2SO4. The CH2Cl2 extract was analyzed by GC-MS (GC, Agilent 6890 series equipped with DB-5 ms column (0.25 mmi.d. 30 cm;MS, Agilent 5973 series). The temperature program for the GC and MS conditions were set according to Hongbin et al. [42]. The acetylated sugar derivatives were identified according to their retention time and the fragmentation pattern of the MS spectrum
	With 5% active carbon-supported ruthenium; hydrogen In water at 140℃; for 1h; Autoclave;
	Multi-step reaction with 2 steps 1: 5% active carbon-supported ruthenium; hydrogen / water / 2 h / 140 °C / 7500.75 Torr / Autoclave 2: 5% active carbon-supported ruthenium; hydrogen / water / 24 h / 140 °C / 7500.75 Torr / Autoclave
	Multi-step reaction with 2 steps 1: 5% active carbon-supported ruthenium; hydrogen / water / 3 h / 140 °C / 7500.75 Torr / Autoclave 2: 5% active carbon-supported ruthenium; hydrogen / water / 24 h / 140 °C / 7500.75 Torr / Autoclave
	Multi-step reaction with 2 steps 1: 5% active carbon-supported ruthenium; hydrogen / water / 3 h / 140 °C / 7500.75 Torr / Autoclave 2: 5% active carbon-supported ruthenium; hydrogen / water / 24 h / 140 °C / 7500.75 Torr / Autoclave
	With ammonium hydroxide; sodium tetrahydroborate

Reference： [1]Glattfeld; Schimpff [Journal of the American Chemical Society, 1935, vol. 57, p. 2204,2206, 2207]
[2]Gaetzi; Reichstein [Helvetica Chimica Acta, 1938, vol. 21, p. 186,188] Delepine; Horeau [Bulletin de la Societe Chimique de France, 1937, vol. <5> 4, p. 1526][Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1937, vol. 204, p. 1605]
[3]Gaetzi; Reichstein [Helvetica Chimica Acta, 1938, vol. 21, p. 186,188] Delepine; Horeau [Bulletin de la Societe Chimique de France, 1937, vol. <5> 4, p. 1526][Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1937, vol. 204, p. 1605]
[4]Ashida [Nippon Nogeikagaku Kaishi, 1949, vol. 23, p. 167][Chem.Abstr., 1950, p. 7780,7781]
[5]Abdel-Akher et al. [Journal of the American Chemical Society, 1951, vol. 73, p. 4691]
[6]Kiliani [Chemische Berichte, 1887, vol. 20, p. 1234,1571]
[7]Holy [Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 10, p. 2786 - 2805]
[8]Nidetzky, Bernd; Brueggler, Kaspar; Kratzer, Regina; Mayr, Peter [Journal of Agricultural and Food Chemistry, 2003, vol. 51, # 27, p. 7930 - 7935]
[9]Location in patent: experimental part Endo, Satoshi; Matsunaga, Toshiyuki; Kuragano, Tsukasa; Ohno, Satoshi; Kitade, Yukio; Tajima, Kazuo; El-Kabbani, Ossama; Hara, Akira [Archives of Biochemistry and Biophysics, 2010, vol. 503, # 2, p. 230 - 237]
[10]Nazifi, Ehsan; Wada, Naoki; Asano, Tomoya; Nishiuchi, Takumi; Iwamuro, Yoshiaki; Chinaka, Satoshi; Matsugo, Seiichi; Sakamoto, Toshio [Journal of Photochemistry and Photobiology B: Biology, 2015, vol. 142, p. 154 - 168]
[11]Van Der Klis, Frits; Gootjes, Linda; Van Haveren, Jacco; Van Es, Daan S.; Bitter, Johannes H. [Green Chemistry, 2015, vol. 17, # 7, p. 3900 - 3909]
[12]Van Der Klis, Frits; Gootjes, Linda; Van Haveren, Jacco; Van Es, Daan S.; Bitter, Johannes H. [Green Chemistry, 2015, vol. 17, # 7, p. 3900 - 3909]
[13]Van Der Klis, Frits; Gootjes, Linda; Van Haveren, Jacco; Van Es, Daan S.; Bitter, Johannes H. [Green Chemistry, 2015, vol. 17, # 7, p. 3900 - 3909]
[14]Van Der Klis, Frits; Gootjes, Linda; Van Haveren, Jacco; Van Es, Daan S.; Bitter, Johannes H. [Green Chemistry, 2015, vol. 17, # 7, p. 3900 - 3909]
[15]Jones, Darryl R.; Uddin, Muhammed Salah; Gruninger, Robert J.; Pham, Thi Thanh My; Thomas, Dallas; Boraston, Alisdair B.; Briggs, Jonathan; Pluvinage, Benjamin; McAllister, Tim A.; Forster, Robert J.; Tsang, Adrian; Selinger, L. Brent; Abbott, D. Wade [Journal of Biological Chemistry, 2017, vol. 292, # 30, p. 12606 - 12620]

2
[ 7643-75-6 ]
[ 108-24-7 ]
1,2,3,4,5-penta-O-acetyl-L-arabinitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	In pyridine for 2h; Ambient temperature;
	With sulfuric acid
	With perchloric acid; acetic acid

	With pyridine
	With 1-methyl-1H-imidazole; acetic acid In water; dimethyl sulfoxide at 20 - 40℃; for 0.166667h;	2.7. Determination of sugars by GC-MS analysis General procedure: To determine the sugars in the glycosylated MAAs, the sugars were released by acid hydrolysis. Following a reduction to alditol, the acetylated derivatives were identified by GC-MS analysis [41]. The purified glycosylated MAA (approximately 20 μg) was hydrolyzedby 5% H2SO4 aq. (100 μL) at 75 °C for 8 h. After hydrolysis the pH was adjusted to 11 with solid Na2CO3. Sodium borohydrate solution (0.5 M in DMSO, 1 ml) was added and kept at 40 °C for 90 min and then incubated at 4 °C overnight to complete reduction. Glacial acetic acid (99.9%, 100 μl), 1-methylimidazole (200 μl) and acetic anhydride (1 ml) were added in this order at room temperature and kept at 40 °C for 10 min. After acetylation we added wate r(2.5 ml) and the acetylated derivatives were extracted by CH2Cl2 (1 ml). An organic phase (lower layer) was recovered and dried with Na2SO4. The CH2Cl2 extract was analyzed by GC-MS (GC, Agilent 6890 series equipped with DB-5 ms column (0.25 mmi.d. 30 cm;MS, Agilent 5973 series). The temperature program for the GC and MS conditions were set according to Hongbin et al. [42]. The acetylated sugar derivatives were identified according to their retention time and the fragmentation pattern of the MS spectrum

Reference： [1]Othman; Al-Timari [Tetrahedron, 1980, vol. 36, # 6, p. 753 - 758]
[2]Abdel-Akher et al. [Journal of the American Chemical Society, 1951, vol. 73, p. 4691]
[3]Abdel-Akher et al. [Journal of the American Chemical Society, 1951, vol. 73, p. 4691]
[4]Rice; Inatome [Journal of the American Chemical Society, 1958, vol. 80, p. 4709]
[5]Nazifi, Ehsan; Wada, Naoki; Asano, Tomoya; Nishiuchi, Takumi; Iwamuro, Yoshiaki; Chinaka, Satoshi; Matsugo, Seiichi; Sakamoto, Toshio [Journal of Photochemistry and Photobiology B: Biology, 2015, vol. 142, p. 154 - 168]

3
[ 7643-75-6 ]
[ 76-83-5 ]
[ 96871-07-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With dmap; triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;
	With pyridine
	With pyridine at 25℃;

Reference： [1]McCaig, Avril E.; Chomier, Berangere; Wightman, Richard H. [Journal of Carbohydrate Chemistry, 1994, vol. 13, # 3, p. 397 - 408]
[2]Valentin [Collection of Czechoslovak Chemical Communications, 1931, vol. 3, p. 507]
[3]Location in patent: scheme or table Ferris, Cristina; De Paz, M. Violante; Galbis, Juan A. [Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 5, p. 1147 - 1154]

4
[ 7643-75-6 ]
(3S,4R)-2-(hydroxymethyl)tetrahydrofuran-3,4-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With sodium dicyanodihydridoborate In trifluoroacetic acid at 100℃; for 40h;

Reference： [1]Garegg, Per J.; Lindberg, Bengt; Konradsson, Peter; Kvarnstroem, Ingemar [Carbohydrate Research, 1988, vol. 176, p. 145 - 148]

5
[ 7643-75-6 ]
1-O-(dichlorophosphite)-2,3:4,5-bis-O-(chlorophosphite)-L-arabitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With phosphorus trichloride In 1,4-dioxane at 60 - 65℃; for 20h;

Reference： [1]Makarova, N. A.; Mukmenev, E. T.; Arbuzov, B. A. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1985, vol. 34, # 4, p. 805 - 808][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1985, # 4, p. 885 - 888]

6
[ 5328-37-0 ]
[ 7643-75-6 ]
(3S,4R)-2-(hydroxymethyl)tetrahydrofuran-3,4-diol [ No CAS ]
[ 32742-34-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 71% 2: 17% 3: 11%	With sodium dicyanodihydridoborate In trifluoroacetic acid at 100℃; for 40h;

Reference： [1]Garegg, Per J.; Lindberg, Bengt; Konradsson, Peter; Kvarnstroem, Ingemar [Carbohydrate Research, 1988, vol. 176, p. 145 - 148]

7
[ 28697-53-2 ]
[ 7643-75-6 ]

Yield	Reaction Conditions	Operation in experiment
90.4%	With sodium tetrahydroborate In methanol for 1h; below 50 deg C;

Reference： [1]Othman; Al-Timari [Tetrahedron, 1980, vol. 36, # 6, p. 753 - 758]

8
[ 7643-75-6 ]
[ 40635-66-3 ]
[ 118227-48-8 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile 1.) 0 deg C, 1.5 h, 2.) RT, 15 h; Yield given;
	In acetonitrile

Reference： [1]Nakatsuka, Masashi; Ragan, John A.; Sammakia, Tarek; Smith, David B.; Uehling, David E.; Schreiber, Stuart L. [Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5583 - 5601]
[2]Schreiber; Sammakia; Uehling [Journal of Organic Chemistry, 1989, vol. 54, # 1, p. 15 - 16]

9
[ 38029-69-5 ]
[ 7643-75-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate In ammonium hydroxide at 30℃; for 2h;

Reference： [1]Pitson, Stuart M.; Voragen, Alphons G.J.; Vincken, Jean-Paul; Beldman, Gerrit [Carbohydrate Research, 1997, vol. 303, # 2, p. 207 - 218]

10
[ 7643-75-6 ]
[ 104196-15-8 ]
[ 51532-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-Phenylbut-1-en-3-one In N,N-dimethyl-formamide at 60 - 80℃; Yield given. Yields of byproduct given;

Reference： [1]Isaac; Aizel; Stasik; Wadouachi; Beaupère [Synlett, 1998, # 5, p. 475 - 476]

11
[ 25636-49-1 ]
[ 7643-75-6 ]
[ 507478-27-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 3,3-dimethoxypentane; L-(-)-arabitol In tetrahydrofuran for 0.25h; Heating / reflux; Stage #2: With chlorosulfonic acid In tetrahydrofuran for 0.0833333h; Heating / reflux; Stage #3: With succinic acid anhydride; triethylamine In dichloromethane for 1.5h; Heating / reflux;	1; 1.a A refluxing suspension of L-arabitol (20.00 g, 131.5 mmol) and 3,3-dimethoxypentane(76.46 g, 578.4 mmol) in THF (200 mL) was stirred for 15 min. CSA (9.16 g,39.4 mmol) was added and the reaction mixture was stirred at reflux for exactly 5 min. EPO The reaction was quenched by addition of NaOH (aq, 2 M, 40 mL) at reflux. Diethylether (50 mL) and water (20 mL) were added and the layers separated. The aqueous phase was extracted with diethylether (3x50 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and the solvent removed in vacuo to give a pale yellow oil. The crude product was dissolved in CH2Cl2 (200 mL) and triethylamine (20 mL) was added. The mixture was heated under reflux and succinic anhydride (3.40 g, 34.0 mmol) was added. The reaction mixture was heated under reflux for 1.5 h, and then quenched with NaHCO3 (aq, sat, 200 mL) at reflux temperature. After cooling the layers were separated and the aqueous layer extracted with CH2Cl2 (2x100 mL). The combined organic phases were washed with brine(100 mL), dried over anhydrous Na2SO4, filtered and evaporated to give a pale yellow oil. Purification by column chromatography (hexane/acetone 80:20) gave (25,45)- l,2:4,5-di-O-(3,3-ρentylidene)arabitol as a pale yellow oil (28.18 g, 74 %). [α]D -5.8 (c 2.50, CHCl3, 25 °C). The 1H and 13C NMR spectra corresponded to the reported data in Linclau B.et al., J. Org. Chem. 2003, 68, 1821.
	With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 38℃;

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2006/89942, 2006, A1 Location in patent: Page/Page column 24-25; 28
[2]Maleczka Jr., Robert E.; Terrell, Lamont R.; Geng, Feng; Ward III, Joseph S. [Organic Letters, 2002, vol. 4, # 17, p. 2841 - 2844]

12
[ 108-30-5 ]
[ 25636-49-1 ]
[ 7643-75-6 ]
[ 507478-27-5 ]
Succinic acid mono-((4S,5S,4'S)-2,2,2',2'-tetraethyl-[4,4']bi[[1,3]dioxolanyl]-5-ylmethyl) ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 3,3-dimethoxypentane; L-(-)-arabitol With camphor-10-sulfonic acid In tetrahydrofuran for 0.0833333h; Heating; Stage #2: succinic acid anhydride With triethylamine In dichloromethane for 1h; Heating;

Reference： [1]Linclau, Bruno; Boydell, A. James; Clarke, Philip J.; Horan, Richard; Jacquet, Claire [Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 1821 - 1826]

13
[ 25636-49-1 ]
[ 7643-75-6 ]
[ 507478-27-5 ]
(2S,3R,4S)-2,3:4,5-di-O-(3,3-pentylidene)arabitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 80% 2: 12%	With camphor-10-sulfonic acid In tetrahydrofuran for 0.0833333h; Heating;
1: 50% 2: 13%	With toluene-4-sulfonic acid In tetrahydrofuran for 4h; Heating;

Reference： [1]Linclau, Bruno; Boydell, A. James; Clarke, Philip J.; Horan, Richard; Jacquet, Claire [Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 1821 - 1826]
[2]Linclau, Bruno; Boydell, A. James; Clarke, Philip J.; Horan, Richard; Jacquet, Claire [Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 1821 - 1826]

14
[ 7643-75-6 ]
[ 77-76-9 ]
[ 84709-35-3 ]
1,2:4,5-di-O-isopropylidene-L-arabitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 58% 2: 9%	With camphor-10-sulfonic acid In acetone at 20℃; for 0.166667h;

Reference： [1]Linclau, Bruno; Boydell, A. James; Clarke, Philip J.; Horan, Richard; Jacquet, Claire [Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 1821 - 1826]

15
[ 6553-96-4 ]
[ 7643-75-6 ]
2,4,6-Triisopropyl-benzenesulfonic acid (2S,3R,4S)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
[ 1053624-50-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 80% 2: 10%	With dmap In pyridine at 0℃; for 24h;

Reference： [1]Leung, Leo M.H.; Gibson, Vicky; Linclau, Bruno [Tetrahedron Asymmetry, 2005, vol. 16, # 14, p. 2449 - 2453]

16
[ 7643-75-6 ]
(2S,4S)-1,5-diazidopentane-2,3,4-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13 mg	Stage #1: L-(-)-arabitol With N,N'-Thionyldiimidazole In tetrahydrofuran at -20℃; for 0.5h; Stage #2: With sodium azide In N,N-dimethyl-formamide at 80℃; for 16h;

Reference： [1]Jang, Jae-Hyuk; Van Soest, Rob W. M.; Fusetani, Nobuhiro; Matsunaga, Shigeki [Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1211 - 1217]

17
[ 7643-75-6 ]
[ 77-76-9 ]
[ 84709-35-3 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In benzene at 75℃; for 14.5h;

Reference： [1]Ichikawa, Yoshiyasu; Yamaoka, Tomonori; Nakano, Keiji; Kotsuki, Hiyoshizo [Organic Letters, 2007, vol. 9, # 16, p. 2989 - 2992]

18
[ 7643-75-6 ]
3,3,3-trifluoro-2-methoxy-2-phenyl-<i>N</i>-[2,3,4-trihydroxy-5-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-pentyl]-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: diimidazolethionyl / tetrahydrofuran / 0.5 h / -20 °C 1.2: 13 mg / NaN₃ / dimethylformamide / 16 h / 80 °C 2.1: 6 mg / ammonium formate / Pd/C / methanol / 0.08 h / 60 °C 3.1: pyridine / 0.17 h / 20 °C 3.2: K₂CO₃ / methanol / 1 h / 20 °C

Reference： [1]Jang, Jae-Hyuk; Van Soest, Rob W. M.; Fusetani, Nobuhiro; Matsunaga, Shigeki [Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1211 - 1217]

19
[ 7643-75-6 ]
3,3,3-trifluoro-2-methoxy-2-phenyl-<i>N</i>-[2,3,4-trihydroxy-5-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-pentyl]-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: diimidazolethionyl / tetrahydrofuran / 0.5 h / -20 °C 1.2: 13 mg / NaN₃ / dimethylformamide / 16 h / 80 °C 2.1: 6 mg / ammonium formate / Pd/C / methanol / 0.08 h / 60 °C 3.1: pyridine / 0.17 h / 20 °C 3.2: K₂CO₃ / methanol / 1 h / 20 °C

Reference： [1]Jang, Jae-Hyuk; Van Soest, Rob W. M.; Fusetani, Nobuhiro; Matsunaga, Shigeki [Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1211 - 1217]

20
[ 7643-75-6 ]
(2S,4S)-1,5-diaminopentane-2,3,4-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: diimidazolethionyl / tetrahydrofuran / 0.5 h / -20 °C 1.2: 13 mg / NaN₃ / dimethylformamide / 16 h / 80 °C 2.1: 6 mg / ammonium formate / Pd/C / methanol / 0.08 h / 60 °C

Reference： [1]Jang, Jae-Hyuk; Van Soest, Rob W. M.; Fusetani, Nobuhiro; Matsunaga, Shigeki [Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1211 - 1217]

21
[ 7643-75-6 ]
(2S,4S)-1,2:4,5-diepoxy-3-pentanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 80 percent / DMAP / pyridine / 24 h / 0 °C 2: 63 percent / NaH / tetrahydrofuran / 1 h / 0 °C
	Multi-step reaction with 2 steps 1: acetonitrile / 1.) 0 deg C, 1.5 h, 2.) RT, 15 h 2: 76 percent / MeONa / tetrahydrofuran / 0.5 h / Ambient temperature

Reference： [1]Leung, Leo M.H.; Gibson, Vicky; Linclau, Bruno [Tetrahedron Asymmetry, 2005, vol. 16, # 14, p. 2449 - 2453]
[2]Nakatsuka, Masashi; Ragan, John A.; Sammakia, Tarek; Smith, David B.; Uehling, David E.; Schreiber, Stuart L. [Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5583 - 5601]

22
[ 7643-75-6 ]
(2S,4S)-1,2:4,5-dianhydro-3-(benzyl)arabitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 80 percent / DMAP / pyridine / 24 h / 0 °C 2.1: NaH / dimethylformamide; diethyl ether / 1 h / 0 °C 2.2: 85 percent / NaI / dimethylformamide; diethyl ether / 24 h / 20 °C
	Multi-step reaction with 2 steps 1.1: pyridine / 0.5 h / 0 °C 2.1: NaH / tetrahydrofuran / 0 °C 2.2: tetrahydrofuran / 16 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: acetonitrile 2: 1.) NaOMe, 2.) NaH

Reference： [1]Leung, Leo M.H.; Gibson, Vicky; Linclau, Bruno [Tetrahedron Asymmetry, 2005, vol. 16, # 14, p. 2449 - 2453]
[2]Smith, Rachel D.; Thomas, Neil R. [Synlett, 2000, # 2, p. 193 - 196]
[3]Schreiber; Sammakia; Uehling [Journal of Organic Chemistry, 1989, vol. 54, # 1, p. 15 - 16]

23
[ 7643-75-6 ]
[ 506418-13-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: camphorsulfonic acid / tetrahydrofuran / 0.08 h / Heating 1.2: 74 percent / Et₃N / CH₂Cl₂ / 1 h / Heating 2.1: 99 percent / SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 6 h / 0 °C
	Multi-step reaction with 2 steps 1: 13 percent / p-toluenesulfonic acid / tetrahydrofuran / 4 h / Heating 2: 99 percent / SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 6 h / 0 °C
	Multi-step reaction with 2 steps 1: CSA / dimethylformamide / 38 °C 2: SO₃*pyridine; i-Pr₂NEt / dimethylsulfoxide / 20 °C

Reference： [1]Linclau, Bruno; Boydell, A. James; Clarke, Philip J.; Horan, Richard; Jacquet, Claire [Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 1821 - 1826]
[2]Linclau, Bruno; Boydell, A. James; Clarke, Philip J.; Horan, Richard; Jacquet, Claire [Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 1821 - 1826]
[3]Maleczka Jr., Robert E.; Terrell, Lamont R.; Geng, Feng; Ward III, Joseph S. [Organic Letters, 2002, vol. 4, # 17, p. 2841 - 2844]

24
[ 7643-75-6 ]
(3E,5E,14E)-(9R,10R,12R,19S,20R)-9,13-Bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dihydroxy-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 19 steps 1.1: CSA / dimethylformamide / 38 °C 2.1: SO₃pyridine; i-Pr₂NEt / dimethylsulfoxide / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 0 °C 4.1: CSA; H₂O / methanol; CH₂Cl₂ / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH₂Cl₂ / 20 °C 6.1: CSA / 40 °C 7.1: TBAF / tetrahydrofuran 8.1: pyridine / CH₂Cl₂ / 0 - 20 °C 9.1: DMP; pyridine / CH₂Cl₂ 10.1: t-BuLi; MgBr₂Et₂O / benzene / 25 h / -78 - 20 °C 10.2: MgBr₂Et₂O / CH₂Cl₂; benzene / 0 °C 11.1: 2,6-lutidine / CH₂Cl₂ / 0 °C 12.1: super-hydride / tetrahydrofuran / 0 °C 13.1: DMP / pyridine / 20 °C 14.1: MgBr₂Et₂O / CH₂Cl₂; benzene 14.2: CH₂Cl₂; benzene; tetrahydrofuran / 0 °C 15.1: NBS; AgNO₃ / acetone / 20 °C 16.1: Bu₃SnF; Red-Sil; TBAF / (PPh₃)2PdCl₂ / diethyl ether / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C 17.1: PhHC=Ru(PCy₃)(IMes-H₂)Cl₂ / CH₂Cl₂ / 40 °C 18.1: 2,6-lutidine / CH₂Cl₂ / 0 °C 19.1: DDQ / 2-methyl-propan-2-ol; CH₂Cl₂; various solvent(s) / 20 °C / pH 7

Reference： [1]Maleczka Jr., Robert E.; Terrell, Lamont R.; Geng, Feng; Ward III, Joseph S. [Organic Letters, 2002, vol. 4, # 17, p. 2841 - 2844]

25
[ 7643-75-6 ]
(3E,5E,14E)-(9R,10R,12R,19S,20R)-9-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-10,12-bis-(4-methoxy-benzyloxy)-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 17 steps 1.1: CSA / dimethylformamide / 38 °C 2.1: SO₃pyridine; i-Pr₂NEt / dimethylsulfoxide / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 0 °C 4.1: CSA; H₂O / methanol; CH₂Cl₂ / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH₂Cl₂ / 20 °C 6.1: CSA / 40 °C 7.1: TBAF / tetrahydrofuran 8.1: pyridine / CH₂Cl₂ / 0 - 20 °C 9.1: DMP; pyridine / CH₂Cl₂ 10.1: t-BuLi; MgBr₂Et₂O / benzene / 25 h / -78 - 20 °C 10.2: MgBr₂Et₂O / CH₂Cl₂; benzene / 0 °C 11.1: 2,6-lutidine / CH₂Cl₂ / 0 °C 12.1: super-hydride / tetrahydrofuran / 0 °C 13.1: DMP / pyridine / 20 °C 14.1: MgBr₂Et₂O / CH₂Cl₂; benzene 14.2: CH₂Cl₂; benzene; tetrahydrofuran / 0 °C 15.1: NBS; AgNO₃ / acetone / 20 °C 16.1: Bu₃SnF; Red-Sil; TBAF / (PPh₃)2PdCl₂ / diethyl ether / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C 17.1: PhHC=Ru(PCy₃)(IMes-H₂)Cl₂ / CH₂Cl₂ / 40 °C

Reference： [1]Maleczka Jr., Robert E.; Terrell, Lamont R.; Geng, Feng; Ward III, Joseph S. [Organic Letters, 2002, vol. 4, # 17, p. 2841 - 2844]

26
[ 7643-75-6 ]
(2E,4E)-(8R,9R,11R)-8-(tert-Butyl-dimethyl-silanyloxy)-12-hydroxy-9,11-bis-(4-methoxy-benzyloxy)-3-methyl-7,10-dimethylene-tetradeca-2,4,13-trienoic acid (1R,2S)-2-methyl-1-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-4-methylene-hept-6-enyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 16 steps 1.1: CSA / dimethylformamide / 38 °C 2.1: SO₃pyridine; i-Pr₂NEt / dimethylsulfoxide / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 0 °C 4.1: CSA; H₂O / methanol; CH₂Cl₂ / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH₂Cl₂ / 20 °C 6.1: CSA / 40 °C 7.1: TBAF / tetrahydrofuran 8.1: pyridine / CH₂Cl₂ / 0 - 20 °C 9.1: DMP; pyridine / CH₂Cl₂ 10.1: t-BuLi; MgBr₂Et₂O / benzene / 25 h / -78 - 20 °C 10.2: MgBr₂Et₂O / CH₂Cl₂; benzene / 0 °C 11.1: 2,6-lutidine / CH₂Cl₂ / 0 °C 12.1: super-hydride / tetrahydrofuran / 0 °C 13.1: DMP / pyridine / 20 °C 14.1: MgBr₂Et₂O / CH₂Cl₂; benzene 14.2: CH₂Cl₂; benzene; tetrahydrofuran / 0 °C 15.1: NBS; AgNO₃ / acetone / 20 °C 16.1: Bu₃SnF; Red-Sil; TBAF / (PPh₃)2PdCl₂ / diethyl ether / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C

Reference： [1]Maleczka Jr., Robert E.; Terrell, Lamont R.; Geng, Feng; Ward III, Joseph S. [Organic Letters, 2002, vol. 4, # 17, p. 2841 - 2844]

27
[ 7643-75-6 ]
(3E,5E,14E)-(9R,10R,12R,19S,20R)-9,13-Bis-(tert-butyl-dimethyl-silanyloxy)-10,12-bis-(4-methoxy-benzyloxy)-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 18 steps 1.1: CSA / dimethylformamide / 38 °C 2.1: SO₃pyridine; i-Pr₂NEt / dimethylsulfoxide / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 0 °C 4.1: CSA; H₂O / methanol; CH₂Cl₂ / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH₂Cl₂ / 20 °C 6.1: CSA / 40 °C 7.1: TBAF / tetrahydrofuran 8.1: pyridine / CH₂Cl₂ / 0 - 20 °C 9.1: DMP; pyridine / CH₂Cl₂ 10.1: t-BuLi; MgBr₂Et₂O / benzene / 25 h / -78 - 20 °C 10.2: MgBr₂Et₂O / CH₂Cl₂; benzene / 0 °C 11.1: 2,6-lutidine / CH₂Cl₂ / 0 °C 12.1: super-hydride / tetrahydrofuran / 0 °C 13.1: DMP / pyridine / 20 °C 14.1: MgBr₂Et₂O / CH₂Cl₂; benzene 14.2: CH₂Cl₂; benzene; tetrahydrofuran / 0 °C 15.1: NBS; AgNO₃ / acetone / 20 °C 16.1: Bu₃SnF; Red-Sil; TBAF / (PPh₃)2PdCl₂ / diethyl ether / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C 17.1: PhHC=Ru(PCy₃)(IMes-H₂)Cl₂ / CH₂Cl₂ / 40 °C 18.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

Reference： [1]Maleczka Jr., Robert E.; Terrell, Lamont R.; Geng, Feng; Ward III, Joseph S. [Organic Letters, 2002, vol. 4, # 17, p. 2841 - 2844]

28
[ 7643-75-6 ]
(3E,5E,14E)-(9R,10R,12R,13R,19S,20R)-9,10,12,13-Tetrahydroxy-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 20 steps 1.1: CSA / dimethylformamide / 38 °C 2.1: SO₃pyridine; i-Pr₂NEt / dimethylsulfoxide / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 0 °C 4.1: CSA; H₂O / methanol; CH₂Cl₂ / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH₂Cl₂ / 20 °C 6.1: CSA / 40 °C 7.1: TBAF / tetrahydrofuran 8.1: pyridine / CH₂Cl₂ / 0 - 20 °C 9.1: DMP; pyridine / CH₂Cl₂ 10.1: t-BuLi; MgBr₂Et₂O / benzene / 25 h / -78 - 20 °C 10.2: MgBr₂Et₂O / CH₂Cl₂; benzene / 0 °C 11.1: 2,6-lutidine / CH₂Cl₂ / 0 °C 12.1: super-hydride / tetrahydrofuran / 0 °C 13.1: DMP / pyridine / 20 °C 14.1: MgBr₂Et₂O / CH₂Cl₂; benzene 14.2: CH₂Cl₂; benzene; tetrahydrofuran / 0 °C 15.1: NBS; AgNO₃ / acetone / 20 °C 16.1: Bu₃SnF; Red-Sil; TBAF / (PPh₃)2PdCl₂ / diethyl ether / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C 17.1: PhHC=Ru(PCy₃)(IMes-H₂)Cl₂ / CH₂Cl₂ / 40 °C 18.1: 2,6-lutidine / CH₂Cl₂ / 0 °C 19.1: DDQ / 2-methyl-propan-2-ol; CH₂Cl₂; various solvent(s) / 20 °C / pH 7 20.1: TBAF; AcOH / tetrahydrofuran / 20 °C

Reference： [1]Maleczka Jr., Robert E.; Terrell, Lamont R.; Geng, Feng; Ward III, Joseph S. [Organic Letters, 2002, vol. 4, # 17, p. 2841 - 2844]

29
[ 7643-75-6 ]
[ 128685-00-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetonitrile / 1.) 0 deg C, 1.5 h, 2.) RT, 15 h 2: 76 percent / MeONa / tetrahydrofuran / 0.5 h / Ambient temperature 3: 84 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) RT, 30 min

Reference： [1]Nakatsuka, Masashi; Ragan, John A.; Sammakia, Tarek; Smith, David B.; Uehling, David E.; Schreiber, Stuart L. [Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5583 - 5601]

30
[ 7643-75-6 ]
[ 128685-01-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetonitrile / 1.) 0 deg C, 1.5 h, 2.) RT, 15 h 2: 76 percent / MeONa / tetrahydrofuran / 0.5 h / Ambient temperature 3: 84 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) RT, 30 min 4: 1.) n-BuLi, 2.) BF₃*OEt₂ / 1.) THF, hexanes, -78 deg C, 30 min, 2.) 1 h

Reference： [1]Nakatsuka, Masashi; Ragan, John A.; Sammakia, Tarek; Smith, David B.; Uehling, David E.; Schreiber, Stuart L. [Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5583 - 5601]

31
[ 7643-75-6 ]
[ 128685-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: acetonitrile / 1.) 0 deg C, 1.5 h, 2.) RT, 15 h 2: 76 percent / MeONa / tetrahydrofuran / 0.5 h / Ambient temperature 3: 84 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) RT, 30 min 4: 1.) n-BuLi, 2.) BF₃OEt₂ / 1.) THF, hexanes, -78 deg C, 30 min, 2.) 1 h 5: 5.2 g / HgCl₂, TsOHH₂O / ethanol / 1.) 12 h, 2.) reflux, 12 h

Reference： [1]Nakatsuka, Masashi; Ragan, John A.; Sammakia, Tarek; Smith, David B.; Uehling, David E.; Schreiber, Stuart L. [Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5583 - 5601]

32
hemicellulose arabinogalactan [ No CAS ]
[ 7296-64-2 ]
[ 7643-75-6 ]
[ 608-66-2 ]
[ 532-20-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; at 184.84℃; under 20 Torr; for 24h;Autoclave;	The hydrolytic hydrogenation experiments were performed in a 300 ml Parr autoclave connected to a pre-reactor with a 200 ml volume. The autoclave was provided with a 1 mum filtered sampling outlet, which prevented the small catalyst particles from passing through it. The temperature was measured with a thermocouple and controlled automatically (Brooks Instrument). 600 mg of arabinogalactan was dissolved in 150 ml of deionized water and loaded to the pre-reactor. 300 mg of the catalyst with a particle size below 63 mum was loaded into the reactor. The amount of the catalyst loading was chosen on the basis of the quantity used in the previous study on the hydrolytic hydrogenation of cellulose [12], in order to facilitate a direct comparison between the hydrolytic hydrogenation of cellulose and hemicelluloses under similar reaction conditions. 20 bar of hydrogen pressure was applied and the solution was heated to 458 K. The stirring rate was 1145 rpm to minimize external diffusion affecting activity measurements. When the reactor had reached the desired temperature, stirring was applied and the arabinogalactan solution from the pre-reactor was fed into the reactor. This was considered as the initial reaction time. Liquid samples were periodically withdrawn at different times for analysis.

Reference： [1]Catalysis Today,2012,vol. 196,p. 26 - 33

33
hemicellulose arabinogalactan [ No CAS ]
[ 98-01-1 ]
[ 67-47-0 ]
[ 7296-64-2 ]
[ 7643-75-6 ]
[ 608-66-2 ]
[ 532-20-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; at 184.84℃; under 20 Torr; for 24h;Autoclave;	The hydrolytic hydrogenation experiments were performed in a 300 ml Parr autoclave connected to a pre-reactor with a 200 ml volume. The autoclave was provided with a 1 mum filtered sampling outlet, which prevented the small catalyst particles from passing through it. The temperature was measured with a thermocouple and controlled automatically (Brooks Instrument). 600 mg of arabinogalactan was dissolved in 150 ml of deionized water and loaded to the pre-reactor. 300 mg of the catalyst with a particle size below 63 mum was loaded into the reactor. The amount of the catalyst loading was chosen on the basis of the quantity used in the previous study on the hydrolytic hydrogenation of cellulose [12], in order to facilitate a direct comparison between the hydrolytic hydrogenation of cellulose and hemicelluloses under similar reaction conditions. 20 bar of hydrogen pressure was applied and the solution was heated to 458 K. The stirring rate was 1145 rpm to minimize external diffusion affecting activity measurements. When the reactor had reached the desired temperature, stirring was applied and the arabinogalactan solution from the pre-reactor was fed into the reactor. This was considered as the initial reaction time. Liquid samples were periodically withdrawn at different times for analysis.

Reference： [1]Catalysis Today,2012,vol. 196,p. 26 - 33

34
[ 7643-75-6 ]
[ 2042-27-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With recombinant Hypocrea jecorina L-arabinitol 4-dehydrogenase; NADH at 25℃; for 2h; Enzymatic reaction;	l-Xylulose production using recombinant HjLAD The initial reaction mixture contained 5 g·L-1 of l-arabinitol and 20 mM of NAD+. To start the reaction, 20 U·mL-1 of purified HjLAD was added. The reaction was performed at 25°C and pH 9.5 or 7.0 in a 3-mL thermoreactor with a stir bar. Samples were withdrawn at constant time intervals and analyzed by the cysteine carbazole sulfuric method and the absorbance was measured at 560 nm.4 The results were further confirmed by HPLC, an Ultimate 3000 high-pressure liquid chromatography system (Dionex, Sunnyvale, CA, USA) equipped with a Shodex sugar sp0810 column (Showa Denko, K. K., Kawasaki, Japan) and an evaporation light scattering detector (ESA6700, Chromachem, MA, USA). Samples were eluted with water at a rate of 1 mL·min-1 at 80°C (column temperature). The nebulizer and evaporation temperatures were 50°C and 65°C, respectively. The retention times for l-arabinitol and l-xylulose were 16.1 and 9.8 min, respectively, at operating conditions (data not shown).

Reference： [1]Tiwari, Manish Kumar; Singh, Raushan Kumar; Gao, Hui; Kim, Taesu; Chang, Suhwan; Kim, Han S.; Lee, Jung-Kul [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 173 - 176]

35
heteropolysaccharide of arabinose, galactose, glucose, rhamnose,and xylose (molar ratio of 3.0:7.0:4.1:1.0:1.5) [ No CAS ]
[ 7643-75-6 ]
[ 87-99-0 ]
[ 488-28-8 ]
[ 50-70-4 ]
[ 608-66-2 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Samples of polysaccharides FCp-1 to FCp-4 (each 5mg) were hydrolyzed in 2M trifluoroacetic acid (TFA; 5mL) at 120C for 6h, and then evaporated to dryness under reduced pressure. The residue was divided into two portions. One portion was used for paper chromatography (PC), which was performed on Whatman 3MM filter paper, eluting with either (a) EtOAc/HOAc/H2O (3:3:1) or (b) n-BuOH/pyridine/H2O (6:4:3) solvent systems. Papers were visualized by aniline-diphenylamine-phosphoric acid solution (a) or p-anisidine solution (b),15 and authentic standards (l-arabinose, d-glucose, d-mannose, d-galactose, d-ribose, d-xylose, l-rhamnose, d-glucuronic acid and d-galactonic acid) were used as reference compounds. The other portion of crude residue was treated with NaBH4 (15mg), and the resulting mixture stirred at room temperature for 12h. The reaction mixture was then treated with a mixture of Ac2O and pyridine (1.0mL of each) at 120 C for 6h,16 and then concentrated to dryness under reduced pressure. The resulting alditol acetates were re-dissolved in CH2Cl2 (1mL) for GC-MS analysis, from which their structures were identified by their retention times and electron-impact profiles.

Reference： [1]Carbohydrate Research,2014,vol. 388,p. 100 - 104

36
[ 7643-75-6 ]
[ 112-85-6 ]
1-O-docosanoylarabitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With Novozym 435 (obtained from NovozymesA/S, Bagsvaerd, Denmark) In <i>tert</i>-butyl alcohol at 60℃; for 24h; Molecular sieve; Enzymatic reaction;

Reference： [1]Wei, Wei; Feng, Fengqin; Perez, Bianca; Dong, Mingdong; Guo, Zheng [Green Chemistry, 2015, vol. 17, # 6, p. 3475 - 3489]

37
[ 58-86-6 ]
[ 7643-75-6 ]
[ 87-99-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 5% active carbon-supported ruthenium; hydrogen In water at 140℃; for 1h; Autoclave;