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[ CAS No. 14686-89-6 ] {[proInfo.proName]}

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Chemical Structure| 14686-89-6
Chemical Structure| 14686-89-6
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Product Details of [ 14686-89-6 ]

CAS No. :14686-89-6 MDL No. :MFCD00069693
Formula : C12H20O6 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 260.28 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 14686-89-6 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.12
TPSA : 66.38 Ų

Pharmacokinetics

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) : -7.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.73
Log Po/w (XLOGP3) : -0.02
Log Po/w (WLOGP) : 0.38
Log Po/w (MLOGP) : -0.06
Log Po/w (SILICOS-IT) : 0.65
Consensus Log Po/w : 0.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.38
Solubility : 11.0 mg/ml ; 0.0422 mol/l
Class : Very soluble
Log S (Ali) : -0.92
Solubility : 31.0 mg/ml ; 0.119 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.6
Solubility : 66.0 mg/ml ; 0.254 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.57

Safety of [ 14686-89-6 ]

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
GHS Pictogram:

Application In Synthesis of [ 14686-89-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 14686-89-6 ]

[ 14686-89-6 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 74-96-4 ]
  • [ 2847-00-9 ]
  • [ 14686-89-6 ]
  • [ 39707-80-7 ]
YieldReaction ConditionsOperation in experiment
68% With magnesium; ethylene dibromide In diethyl ether at -30℃; for 2h;
  • 2
  • [ 4143-60-6 ]
  • [ 14686-89-6 ]
  • [ 82893-15-0 ]
YieldReaction ConditionsOperation in experiment
45% With tetra-n-butylammonium cyanide; triphenylphosphine; methyl trifluoromethanesulfonate In toluene at 50℃; for 2h;
  • 3
  • [ 14686-89-6 ]
  • [ 821-09-0 ]
  • [ 141943-49-9 ]
YieldReaction ConditionsOperation in experiment
70% With hydrogenchloride In acetone at 60℃; for 2h;
  • 5
  • [ 14686-89-6 ]
  • [ 142330-81-2 ]
  • [ 128190-40-9 ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine In dichloromethane for 0.166667h; Ambient temperature;
  • 7
  • [ 14686-89-6 ]
  • [ 14049-05-9 ]
YieldReaction ConditionsOperation in experiment
88% With pyridine; diethylamino-sulfur trifluoride In dichloromethane
71.5% With pyridine; diethylamino-sulfur trifluoride In dichloromethane for 15h; Ambient temperature;
64% With dmap; diethylamino-sulfur trifluoride In dichloromethane 1) -20 deg C, 15 min, 2) RT, 24 h;
53% With diethylamino-sulfur trifluoride
Multi-step reaction with 2 steps 1: 90 percent / pyridine / CH2Cl2 / 2 h / -20 °C 2: 43 percent / cesium fluoride / DMF, reflux, 30 min then petroleum ether, reflux, 15 min
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 2: tris(dimethylamino)sulfonium difluorotrimethylsilicate / CH2Cl2 / 0.17 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: pyridine 2: potassium fluoride / various solvent(s) / 200 °C

  • 8
  • [ 2847-00-9 ]
  • [ 14686-89-6 ]
YieldReaction ConditionsOperation in experiment
92% With sodium tetrahydroborate In ethanol; water
85% With sodium tetrahydroborate In tetrahydrofuran
81% With sodium tetrahydroborate In methanol
With sodium tetrahydroborate In ethanol; water at 2℃; for 1.5h; Yield given;
With sodium tetrahydroborate
With sodium tetrahydroborate
With sodium tetrahydroborate In ethanol at 2℃; for 1.5h;
1.35 g With sodium tetrahydroborate In ethanol; water
With sodium tetrahydroborate In ethanol; water for 5h; Ambient temperature; Yield given;
With sodium tetrahydroborate In ethanol Yield given;
With sodium tetrahydroborate Yield given;
With sodium tetrahydroborate; ethanol; water at -20 - 0℃; for 0.5h;
With sodium tetrahydroborate In ethanol; water for 3h; Ambient temperature; Yield given;
With sodium tetrahydroborate In ethanol; water at 0℃; for 1h; Yield given;
With sodium tetrahydroborate In ethanol
With sodium tetrahydroborate; acetic anhydride 1.) pyridine, reflux, 2.) EtOH; Multistep reaction;
Multi-step reaction with 3 steps 1: 90 percent / pyridine / 10 h / Heating 2: 98 percent / H2 / Pd-C / ethyl acetate / 20 h / 20 °C / 1810.02 Torr 3: 99 percent / H2O; triethylamine / methanol / 3 h / 20 °C
Multi-step reaction with 3 steps 1: pyridine 2: H2 / Pd black / ethyl acetate 3: K2CO3 / methanol
Multi-step reaction with 3 steps 1.1: diethyl ether; water / 7 h / Reflux 1.2: 75 °C 2.1: palladium on activated charcoal; hydrogen / methanol / 120 h / 20 °C 3.1: sodium methylate / methanol / 3 h / 20 °C / pH 9.5
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose With pyridine; acetic anhydride Inert atmosphere; Stage #2: With palladium on activated charcoal; hydrogen Inert atmosphere; Stage #3: With sodium hydroxide Inert atmosphere; diastereoselective reaction;

Reference: [1]Drueckhammer, Dale G.; Wong, Chi-Huey [Journal of Organic Chemistry, 1985, vol. 50, # 26, p. 5912 - 5913]
[2]Le Diguarher, Thierry; Boudon, Alain; Elwell, Claire; Paterson, Duncan E.; Billington, David C. [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 16, p. 1983 - 1988]
[3]Reckendorf, Wolfgang Meyer zu; Schultz, Norbert; Kreimeier, Richard [Liebigs Annalen der Chemie, 1994, # 4, p. 337 - 346]
[4]Yoshikawa; Okaichi; Cha; Kitagawa [Tetrahedron, 1990, vol. 46, # 21, p. 7459 - 7470]
[5]Cote; Robyt [Carbohydrate research, 1982, vol. 101, # 1, p. 57 - 74]
[6]Nicolaou; Pavia; Seitz [Journal of the American Chemical Society, 1982, vol. 104, # 7, p. 2027 - 2029]
[7]Yoshikawa; Okaichi; Cha; Kitagawa [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 9, p. 2555 - 2557]
[8]Ikekawa; Irinoda; Saze; Katori; Matsuda; Ohkawa; Kosik [Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 7, p. 2894 - 2899]
[9]Argentini, M.; Weinreich, R.; Oberti, Roberta; Ungaretti, Luciano [Journal of Fluorine Chemistry, 1986, vol. 32, p. 239 - 254]
[10]Li; Han; Joullie [Tetrahedron, 1993, vol. 49, # 4, p. 785 - 802] Li, Wen-Ren; Han, So-Yeop; Joullie, Madeleine M. [Tetrahedron Letters, 1992, vol. 33, # 25, p. 3595 - 3598]
[11]Wood, William W.; Watson, Graham M. [Journal of the Chemical Society. Chemical communications, 1986, # 21, p. 1599 - 1600]
[12]Bichard, Claire J. F.; Wheatley, Joseph R.; Fleet, George W. J. [Tetrahedron Asymmetry, 1994, vol. 5, # 3, p. 431 - 440]
[13]Pitsch, Stefan [Helvetica Chimica Acta, 1997, vol. 80, # 8, p. 2286 - 2314]
[14]Estevez, Juan C.; Fairbanks, Antony J.; Fleet, George W.J. [Tetrahedron, 1998, vol. 54, # 44, p. 13591 - 13620]
[15]Chen; Guo; Liu [Journal of the American Chemical Society, 1998, vol. 120, # 38, p. 9951 - 9952]
[16]Trifonova, Anna; Foeldesi, Andras; Dinya, Zoltan; Chattopadhyaya, Jyoti [Tetrahedron, 1999, vol. 55, # 15, p. 4747 - 4762]
[17]Elhalabi, Jordan; Rice, Kevin G. [Nucleosides, nucleotides and nucleic acids, 2004, vol. 23, # 1-2, p. 195 - 205]
[18]Watterson, Mark P.; Pickering, Lea; Smith, Martin D.; Hudson, Sarah J.; Marsh, Paul R.; Mordaunt, Jacqueline E.; Watkin, David J.; Newman, Christopher J.; Fleet, George W. J. [Tetrahedron Asymmetry, 1999, vol. 10, # 10, p. 1855 - 1859]
[19]Hoffmann-Roeder, Anja; Johannes, Manuel [Chemical Communications, 2011, vol. 47, # 35, p. 9903 - 9905]
[20]Turks, Maris; Věze, Krista; Kiseļovs, Gļebs; Mackeviča, Jevgeņija; Lugiņina, Jevgeņija; Mishnev, Anatoly; Marković, Dean [Carbohydrate Research, 2014, vol. 391, # 1, p. 82 - 88]
  • 9
  • 1,2,5,6-di-O-isopropylidene-3-O-(p-toluenesulfonyl)-α-D-allofuranose [ No CAS ]
  • [ 14686-89-6 ]
YieldReaction ConditionsOperation in experiment
95% With base In methanol Irradiation;
65% With hydrazine In water; acetonitrile for 2h; Ambient temperature;
  • 10
  • [ 14686-89-6 ]
  • [ 358-23-6 ]
  • [ 74925-16-9 ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane for 15h; Ambient temperature;
With pyridine
With pyridine In dichloromethane at -10℃; for 1h;
With pyridine In dichloromethane at -20℃; for 0.5h; 9.5-9.6 Step~5 and 6 : (3aR,5R,6S,6aR)-6-azido-5-((R)-2,2-dimethyl-1 ,3-dioxolan-4~yl)-2,2- dimethyi tetrahydrofuro[2,3-d][1 ,3]dioxole: [00272] To a stirred solution of SaR.SR^R.eaRJ-S-^R^^-dimetbyl- S- dioxoian-4-yi)-2,2-dimethyltetra hydrofuro[2,3-d][1 ,3]dioxo-6-o (510 g) in DC :pyridine (3.0 eq) was slowly added triflic anhydride in DCM at -20 °C and the reaction mixture was stirred at same temperature for 30 min. after completion, the reaction mixture was quenched with ice cold 1 N HCi (pH ~ 8) and the aqueous layer was extracted with DCM (2 x 1000 mL), dried (Na2S04) and concentrated. This crude residue was dissolved in DMF and NaN3 (5.0 eq) was added portionwise at 0 °C and stirred at the same temperature for 3 h. After completion, the reaction mixture was poured into ice water (500 mL) and extracted with ethyl acetate (2 x 1000 mL). The combined organic layer was again washed with ice cold water (3 x 500 mL), dried (Na2S04) and concentrated. The residue was purified by flash column chromatography [normal phase, silica gel (100-200 mesh), gradient 0 to 5% EtOAc in hexane] to afford the title compound as pale yellow gum (150 g, 27%). 1 H N R (400 MHz, CDCI3): L 5.80 (d, J = 3.8 Hz, 1 H), 4.60 - 4.63 (m, 1 H) 4.35 - 4.39 (m, 1 H), 4.10 (t, J = 3.6 Hz, 1 H), 3.94 (d, J = 2.8 Hz, 1 H), 3.89 - 3.93 (m, 2H), 1 .58 (s, 3H), 1 .55 (s, 3H), 1 .45 (s, 3H), 1 .36 (s, 3H).
With pyridine In tert-butyl methyl ether at 5 - 10℃; for 3h; Alternative process To a solution of l,2:5,6-di-0-isopropylidene-a-D-gulofuranose, VI (200 g, 0.77 mol) in TBME (540 mL) pyridine (112 mL, 1.84 mol) was added and the solution cooled to 5 °C. Trifluoromethanesulfonic anhydride (262 g, 0.93 mol) was added over 2 hours to the suspension maintaining 5 °C followed by TBME (72 mL). The reaction mixture was warmed to 10 °C and stirred for 1 hour then quenched by addition of sodium bisulphite solution [made from pre-mixed 50% aqueous NaOH (22.0 g), water (138 mL) and 95% sulphuric acid (56 g)] at 5 °C. Water (140 mL) was added and the mixture warmed to 20 °C. The layers were separated and the organic phase washed with water (140 mL), 5% aqueous NaHCCb solution (140 mL) then 18% aqueous NaCl solution (128 mL) at 20 °C. The layers were separated and triethylamine hydrochloride (80 g, 0.58 mol) and tetrabutyl ammonium bromide (TBAB) (24.0 g, 0.16 mol) added to the organic phase. Sodium azide (74 g, 1.14 mol) dissolved in water (200 mL) was added at 20 °C then the mixture heated to 50 °C. The reaction was held for 20 hours then cooled to 20 °C and water (400 mL) added. The phases were separated and the organic phase washed with water (200 mL) then 18% aqueous sodium chloride (120 mL). A solvent exchange to 2-methyl tetrahydrofuran (2-MeTHF)was performed through distillation in vacuo at up to 60°C. 3-azido-3-deoxy-l,2:5,6-di-0-isopropylidene-a-D-galactofuranose VIII (206 g, 94% th over two steps from VI) was progressed to the manufacture of l,2,4,6-Tetra-0-acetyl-3- azido-3-deoxy-P-D-galactopyranose X, as a solution in 2-MeTHF, ca. 840 mL total volume.

  • 11
  • [ 14686-89-6 ]
  • [ 22435-76-3 ]
YieldReaction ConditionsOperation in experiment
89.3% With dmap; diethylamino-sulfur trifluoride In dichloromethane for 24h; Ambient temperature;
84% With dmap; diethylamino-sulfur trifluoride In dichloromethane at -10 - 20℃; for 48h;
63% With dmap; diethylamino-sulfur trifluoride In dichloromethane at 20℃; for 24h; Inert atmosphere; Cooling;
With diethylamino-sulfur trifluoride
With 4,4'-diaminostilbene-2,2'-disulfonic acid
Multi-step reaction with 2 steps 1: 92 percent / pyridine / 60 °C 2: 1) dehydrated Amberlyst-A-26 (F(-)) resin; 2) H2, NaHCO3 / 2) 5percent Pd-on-charcoal / 1) benzene, reflux; 2) EtOH, 1 Atm, room temp., 30 min

  • 12
  • [ 14686-89-6 ]
  • [ 19131-08-9 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: (1,2:5,6)-di-O-isopropylidene-D-gulose With pyridine; trifluoromethylsulfonic anhydride In dichloromethane for 0.5h; Cooling with ice; Stage #2: With trimethylsilylazide; sodium fluoride In N,N-dimethyl-formamide at 50℃; 3-5 Example 3 General procedure: Compound I (29.9g, 114.88mmol) was dissolved in dichloromethane (100mL), pyridine (27.81mL, 344.6mmol) was added, after cooling to the ice bath temperature, trifluoromethanesulfonic anhydride (38.6mL, 229.7mmol) was added dropwise, After stirring for 30 min under ice bath, TLC (PE:EA=1:1) showed that the reaction was complete. The reaction solution was washed with 1N HCla.q., sat.NaHCO3a.q. and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The brown syrup intermediate is obtained, which is directly used in the next reaction;Azidotrimethylsilane (52.9mL, 402.1mmol) and sodium fluoride (15.9g, 379.1mmol) were mixed in DMF (150mL), refluxed in an oil bath at 100°C for 1 hour, cooled to room temperature, and added The DMF solution of the brown syrup intermediate obtained in the step reaction, the mixture was refluxed overnight in an oil bath at 50°C, TLC (PE:EA=1:1) detected that the reaction was complete, the reaction solution was cooled to room temperature, poured into water, and the mixture was subjected to dichloromethane Methane extraction three times (3*300mL), combine the organic phases, wash with brine, dry with anhydrous sodium sulfate, concentrate and mix the sample, separate by column chromatography (PE:EA=6:1) to obtain colorless syrup II, which will solidify after standing for a long time (29.64g, 90.2%).
73% With tris-(2-chloro-ethyl)-amine; thiamine diphosphate; diethylazodicarboxylate In benzene at 60℃; for 0.5h;
Multi-step reaction with 2 steps 1: pyridine 2: NaN3 / dimethylformamide
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / 15 h / Ambient temperature 2: sodium azide / dimethylformamide / 2 h
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0.5 h / -20 °C 2: sodium azide / N,N-dimethyl-formamide / 3 h / 0 °C
Multi-step reaction with 2 steps 1: pyridine / tert-butyl methyl ether / 3 h / 5 - 10 °C 2: sodium azide; triethylamine hydrochloride; tetrabutylammomium bromide / tert-butyl methyl ether; water / 20 h / 50 °C

  • 13
  • [ 26775-14-4 ]
  • [ 14686-89-6 ]
YieldReaction ConditionsOperation in experiment
100% With methanol; sodium methylate for 2h;
99% With water; triethylamine In methanol at 20℃; for 3h;
96% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
94% With sodium methylate In methanol Ambient temperature;
94% With sodium methylate In methanol at 20℃; for 3h;
91% With sodium methylate In methanol for 0.5h; Ambient temperature;
89% With sodium methylate In methanol at 20℃; for 0.5h;
With potassium carbonate In methanol
With methanol; sodium methylate at 0℃; for 3h; 5.c Sodium methoxide (12.5 g) was added to a solution of compound (64 g), obtained from step b above, in methanol (10 mL). The reaction mixture was stirred for 3 hours at 00C. The reaction mixture was then concentrated. The residue thus obtained was purified by column chromatography over silica gel using 30 % ethyl acetate in hexane as eluant to afford the title compound (31 g). Mass (m/z): 261.26 (M+ +1)
With water; triethylamine In methanol at 20℃; for 3.5h; 9.4 Step~4: (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1 ,3-dioxolan-4-yl)-2,2- dimethyltefra hydrofuro[2,3-d][1 ,3]dioxoi-6-ol: To a stirred solution of (3aR,5S,6R,6aR)-5-((R)-2,2-dimethyl-1 ,3-dioxoian-4-yi)~2,2-dimethy tetrahydrofuro [2,3-d][1 ,3]dioxol-6-yl acetate (544.0 g) in MeOH : H20 (1900 mL: 190Q mL) was added Et3N (3,0 eq) and the reaction mixture was stirred at rt for 3.5 h. After completion, the reaction mixture was concentrated in vacuum and codistilied with toluene (3 x 500 mL) to afford the title compound as a black solid (510 g, crude). The crude was used for next step without purification. 1 H NMR (400 MHz; CDCI3): L 5.78 (d, J = 4,0 Hz, 1 H), 4.66 (t, J = 10.2 Hz, 1 H), 4.44 - 4.50 (m, 1 H), 4.2 (m, 1 H), 3.9 ( m, 1 H), 3.03 - 3.09 (m, 1 H), 3.70 (t, J = 4.5 Hz, 1 H), 1 .44 (s, 3H), 1 .42 (s, 3H), 1 .37 (s, 3H).
0.60 kg With sodium methylate In methanol at 20℃; for 1h; l,2:5,6-di-0-Isopropylidene-a-D-gulofuranose, VI To a solution of 3-O-acetyl- 1,2:5, 6-di-O-isopropylidene-a-D-gulofuranose, V (3.33 mol) in methanol at rt was charged a solution of 25 wt% sodium methoxide in methanol to pH 11. The reaction mixture was stirred at rt for 1 hour, followed by the addition of solid carbon dioxide until the pH was < 7.5. The mixture was concentrated in vacuo at 40 °C using a rotary evaporator and the crude residue was suspended in ethyl acetate (3.9 L) and heated to 60 °C. The mixture was allowed to cool to < 40 °C then filtered, washing with ethyl acetate (1.5 L). The mixture was concentrated in vacuo at 40 °C to a volume of 2.5 L and heated to 60 °C. Heptane (4.65 L) was added and the mixture cooled from 60 °C to 5 °C and stirred for 30 minutes. The product was isolated by filtration washing with heptane (3 x 0.5 L). The filter cake was dried under vacuum at 40 °C to give 0.60 kg (47% over 4 steps from P) of l,2:5,6-di- O-isopropylidene-a-D-gulofuranose as an off-white solid. 'H NMR (400 MHz, CDCli) d 5.78 (d, J= 4.1 Hz, 1H), 4.66 (dd, J= 6.3, 4.1 Hz, 1H), 4.52 - 4.43 (m, 1H), 4.26 - 4.19 (m, 2H), 3.90 (dd, J= 8.6, 5.7 Hz, 1H), 3.72 (dd, J= 8.6, 7.2 Hz, 1H), 2.64 (d, J= 6.4 Hz, 1H), 1.63 (s, 3H), 1.45 (s, 3H), 1.43 (s, 3H),1.38 (s, 3H).

Reference: [1]Raju, Ravinder; Castillo, Bernard F.; Richardson, Stewart K.; Thakur, Meena; Severins, Ryan; Kronenberg, Mitchell; Howell, Amy R. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4122 - 4125]
[2]Elhalabi, Jordan; Rice, Kevin G. [Nucleosides, nucleotides and nucleic acids, 2004, vol. 23, # 1-2, p. 195 - 205]
[3]Location in patent: experimental part Bhujbal, Namdeo N.; Kumar, K. S. Ajish; Dhavale, Dilip D. [Synthesis, 2009, # 14, p. 2423 - 2429]
[4]Sharma, G. V. M.; Rao, S. Mahender [Tetrahedron Letters, 1992, vol. 33, # 17, p. 2365 - 2368]
[5]Hoffmann-Roeder, Anja; Johannes, Manuel [Chemical Communications, 2011, vol. 47, # 35, p. 9903 - 9905]
[6]Schmid, Walther; Zbiral, Erich [Monatshefte fur Chemie, 1983, vol. 114, p. 1253 - 1258]
[7]Malatinský, Tomáš; Spišáková, Mária; Babjak, Matej; Doháňošová, Jana; Marek, Jaromír; Moncol, Ján; Fischer, Róbert [European Journal of Organic Chemistry, 2017, vol. 2017, # 6, p. 1086 - 1098]
[8]Watterson, Mark P.; Pickering, Lea; Smith, Martin D.; Hudson, Sarah J.; Marsh, Paul R.; Mordaunt, Jacqueline E.; Watkin, David J.; Newman, Christopher J.; Fleet, George W. J. [Tetrahedron Asymmetry, 1999, vol. 10, # 10, p. 1855 - 1859]
[9]Current Patent Assignee: SUN PHARMACEUTICAL INDUSTRIES LIMITED - WO2008/23336, 2008, A2 Location in patent: Page/Page column 81
[10]Current Patent Assignee: GALECTIN THERAPEUTICS INC - WO2018/209276, 2018, A1 Location in patent: Paragraph 00268-00269
[11]Current Patent Assignee: GALECTO BIOTECH AB - WO2021/198160, 2021, A1 Location in patent: Page/Page column 12
  • 14
  • [ 14686-89-6 ]
  • [ 100-39-0 ]
  • [ 22331-21-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride 1.) DMF, room temp., 2 h 2.) DMF, room temp., 2 h; Yield given. Multistep reaction;
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran for 2h; Ambient temperature;
With sodium hydride 1) THF, 1 h, reflux, 2) 1 h, reflux; Yield given. Multistep reaction;
With tetra-(n-butyl)ammonium iodide; sodium hydride 1) THF, r.t., 45 min, 2) reflux, 1 h; Yield given. Multistep reaction;
With tetra-(n-butyl)ammonium iodide; sodium hydride
With tetra-(n-butyl)ammonium iodide; sodium hydride 1.) THF, 2.) THF, RT, 3 h; Yield given. Multistep reaction;
With sodium hydride 1.) THF, from 0 deg C to RT, 2.) THF, reflux, 1 h; Multistep reaction;
With sodium hydride In N,N-dimethyl-formamide for 1h; Ambient temperature; Yield given;
With sodium hydride
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 0 - 25℃;

  • 15
  • [ 14686-89-6 ]
  • [ 103-72-0 ]
  • [ 165589-86-6 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydride In tetrahydrofuran
  • 17
  • [ 14686-89-6 ]
  • [ 824-94-2 ]
  • 3-O-(4-Methoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran for 12h; Ambient temperature;
With sodium hydride In tetrahydrofuran for 48h; Heating; Yield given;
With sodium hydride In tetrahydrofuran
  • 18
  • [ 14686-89-6 ]
  • [ 98-59-9 ]
  • 1,2,5,6-di-O-isopropylidene-3-O-(p-toluenesulfonyl)-α-D-allofuranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane Ambient temperature;
With pyridine
  • 19
  • [ 14686-89-6 ]
  • [ 77-76-9 ]
  • [ 55520-70-2 ]
YieldReaction ConditionsOperation in experiment
76% With hydrogenchloride In methanol; acetone for 2h; Heating;
  • 20
  • [ 14686-89-6 ]
  • [ 98-58-8 ]
  • [ 88405-99-6 ]
YieldReaction ConditionsOperation in experiment
92% In pyridine at 60℃;
  • 21
  • [ 582-52-5 ]
  • [ 14686-89-6 ]
YieldReaction ConditionsOperation in experiment
With ruthenium trichloride; sodium tetrahydroborate; potassium metaperiodate; Celite; ammonium chloride; potassium carbonate 1.) chloroform, water 3.) MeOH, 0 deg C, 20 min 4.) r.t., 2 h 5.) 20 min; Yield given. Multistep reaction;
With sodium tetrahydroborate; pyridinium chlorochromate 1.) dichloromethane, room temperature, 3 h 2.) ethanol, water, 0 deg C, 1 h; Yield given. Multistep reaction;
With sodium tetrahydroborate; acetic anhydride 1.) DMSO, 70 deg C, 2.) EtOH, 0 deg C -> room temperature; Yield given. Multistep reaction;
With sodium tetrahydroborate; acetic anhydride; dimethyl sulfoxide Yield given. Multistep reaction;
Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 24 h 2: sodium borohydide, ethanol, water / 0.5 h / -20 - 0 °C
Multi-step reaction with 2 steps 1: acetic anhydride / dimethylsulfoxide / 2 h / 70 °C 2: sodium borohydride / ethanol; H2O / 5 h / Ambient temperature
Multi-step reaction with 3 steps 1: 65 percent / pyridine / 16 h / 75 °C 2: 90 percent / H2 / Pd / diethyl ether / 24 h 3: 91 percent / CH3ONa / methanol / 0.5 h / Ambient temperature
Multi-step reaction with 2 steps 1: pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 2: 1.35 g / sodium borohydride / ethanol; H2O
Multi-step reaction with 2 steps 1: chromium trioxide, pyridine 2: sodium borohydride
Multi-step reaction with 4 steps 1: NaH / tetrahydrofuran / 20 °C 2: 57 percent Chromat. / CF3CO3H, Na2HPO4 / CH2Cl2 / 0 - 20 °C 3: CuSO4 / 24 h / 20 °C 4: 37 percent / KO2, 18C6, / dimethylsulfoxide
Multi-step reaction with 3 steps 1: NaH / tetrahydrofuran / 20 °C 2: KMnO4, NaOH, TEBA-Br / tetrahydrofuran; H2O / 2 h / 20 °C 3: 37 percent / KO2, 18C6, / dimethylsulfoxide
Multi-step reaction with 2 steps 1: 3.20 g / (COCl)2, DMSO / CH2Cl2 / 1 h / -78 °C 2: NaBH4 / ethanol; H2O / 1.5 h / 2 °C
Multi-step reaction with 2 steps 1.1: acetic anhydride; dipyridinium dichromate / 20 °C 1.2: 90 °C 2.1: palladium on activated charcoal; hydrogen / ethyl acetate / 3 h / 2068.65 Torr 2.2: 0.5 h / 20 °C / pH 8 - 10
Multi-step reaction with 4 steps 1: water; sodium bromide; sodium acetate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / ethyl acetate / 8.5 h / 3 - 7 °C / pH 11.5 - 12.5 / Large scale 2: pyridine / 16 h / 20 - 60 °C / Large scale 3: triethylsilane; palladium 10% on activated carbon; methanol / 20 - 35 °C / Large scale 4: sodium methylate / methanol / 1 h / 20 °C / pH 11

Reference: [1]Wood, William W.; Watson, Graham M. [Journal of the Chemical Society. Perkin transactions I, 1987, p. 2681 - 2688]
[2]Austin, Geoffrey N.; Baird, Peter D.; Fleet, George W. J.; Peach, Josephine M.; Smith, Paul W.; Watkin, David J. [Tetrahedron, 1987, vol. 43, # 13, p. 3095 - 3108]
[3]Han, So-Yeop; Liddell, Paul A.; Joullie, Madeleine M. [Synthetic Communications, 1988, vol. 18, # 3, p. 275 - 284]
[4]Specha, Maurus [Helvetica Chimica Acta, 1993, vol. 76, p. 1832 - 1846]
[5]Barton, Derek H.R.; Jaszberenyi, Joseph Cs.; Theodorakis, Emmanouil A. [Journal of the American Chemical Society, 1992, vol. 114, # 14, p. 5904 - 5905]
[6]Bichard, Claire J. F.; Wheatley, Joseph R.; Fleet, George W. J. [Tetrahedron Asymmetry, 1994, vol. 5, # 3, p. 431 - 440]
[7]Argentini, M.; Weinreich, R.; Oberti, Roberta; Ungaretti, Luciano [Journal of Fluorine Chemistry, 1986, vol. 32, p. 239 - 254]
[8]Schmid, Walther; Zbiral, Erich [Monatshefte fur Chemie, 1983, vol. 114, p. 1253 - 1258]
[9]Ikekawa; Irinoda; Saze; Katori; Matsuda; Ohkawa; Kosik [Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 7, p. 2894 - 2899]
[10]Cote; Robyt [Carbohydrate research, 1982, vol. 101, # 1, p. 57 - 74]
[11]Netscher, Thomas [Tetrahedron Letters, 1988, vol. 29, # 4, p. 455 - 458]
[12]Netscher, Thomas [Tetrahedron Letters, 1988, vol. 29, # 4, p. 455 - 458]
[13]Yoshikawa; Okaichi; Cha; Kitagawa [Tetrahedron, 1990, vol. 46, # 21, p. 7459 - 7470]
[14]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Shenzhen Institute of Advanced Technology (in: CAS) - CN112745372, 2021, A
[15]Current Patent Assignee: GALECTO BIOTECH AB - WO2021/198160, 2021, A1
  • 22
  • [ 14686-89-6 ]
  • [ 2373-51-5 ]
  • [ 106180-04-5 ]
YieldReaction ConditionsOperation in experiment
62% With sodium hydride In 1,4-dioxane Ambient temperature;
  • 23
  • [ 14686-89-6 ]
  • [ 106-95-6 ]
  • [ 33746-39-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide; tetrabutylammomium bromide In dichloromethane for 2h;
93% With sodium hydride In N,N-dimethyl-formamide
90% With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran for 24h; Ambient temperature;
  • 24
  • [ 14686-89-6 ]
  • [ 18422-58-7 ]
YieldReaction ConditionsOperation in experiment
87% With periodic acid In ethyl acetate for 2h;
  • 25
  • [ 14686-89-6 ]
  • [ 814-68-6 ]
  • [ 214417-54-6 ]
YieldReaction ConditionsOperation in experiment
40% With triethylamine In dichloromethane at -20 - 20℃; for 6.5h;
  • 26
  • [ 14686-89-6 ]
  • [ 85920-63-4 ]
  • [ 342003-63-8 ]
  • 27
  • [ 14686-89-6 ]
  • [ 26623-13-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (1,2:5,6)-di-O-isopropylidene-D-gulose With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium acetate; potassium bromide In water; ethyl acetate for 0.333333h; Stage #2: With triethylamine In water; ethyl acetate for 0.5h; 5.d Sodium hypochlorite (225 mL, 4% solution) was added dropwise to a solution compound (30 g), obtained from step c above, followed by addition of 2,2,6,6,- tetramethylpiperidine N-oxyl (0.18 g), potassium bromide (10.62 g) and sodium acetate (14.19 g) in ethyl acetate (300 mL) and water (100 mL). After 20 min, triethylamine (3.3 mL) was added dropwise to the above mixture at the same temperature. The reaction mixture was extracted with ethyl acetate after 30 min. The organic layer was dried over anhydrous sodium sulphate. The solvent was evaporated under the reduced pressure to afford the title compound (10.4 g).
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In dichloromethane; water at -10℃; 5 In an open-mouth beaker, a solution of NaBr (0.4 g, 3.89 mmol, 0.1 equiv) in water (2 mL) was added to a solution of diacetone-α-d-gulose (8) (10.0 g, 38.4 mmol, 1.0 equiv) in CH2Cl2 (40 mL) and followed by TEMPO (30 mg, 0.19 mmol, 0.5 mol %). The resulting mixture was cooled to -10 °C (internal temperature), vigorously stirred, and an aqueous solution of NaClO (∼1.6 mol/L, 50 mL, 80 mmol, 2.1 equiv; pH adjusted with NaHCO3 to 9.5) was added drop-wise while keeping the internal temperature at -5 to 0 °C. After addition of the bleach solution, the resulting reaction mixture was stirred for 5 min, the organic layer separated, and washed successively with a solution of KI (0.1 g, 0.6 mmol, 1.6 mol %) in 0.5 M aqueous sulfuric acid (15 mL), a 10% aqueous solution of Na2S2O3 (15 mL), a saturated aqueous solution of NaHCO3 (20 mL), and brine (20 mL). The organic layer was dried (Na2SO4), filtered, evaporated under reduced pressure, and product 9 obtained as a yellowish solid (8.0 g, 80%, purity by NMR ⩾95%).Product 9 was used in the next step without additional purification. The NMR data and other characteristics of product 9 fully corresponded to those reported earlier.16 Rf = 0.37 (Tol/EtOAc = 13:7); mp 69-70 °C; 1H NMR (CDCl3, 300 MHz) δ, ppm: 6.05 (d, 1H, 3J = 4.3 Hz, H-C(1)), 4.45 (d, 1H, 3J = 4.3 Hz, H-C(2)), 4.33 (q, 1H, 3J = 6.6 Hz, H-C(5)), 4.11 (d, 1H, 3J = 6.6 Hz, H-C(4)), 4.09 (dd, 1H, 2J = 8.9 Hz, 3J = 6.6 Hz, Ha-C(6)), 4.02 (dd, 1H, 2J = 8.9 Hz, 3J = 6.6 Hz, Hb-C(6)), 1.54, 1.44, 1.40, 1,36 (4s, 12H, (H3C)2C-O-C(1,2,5,6)). 13C NMR (CDCl3, 100.6 MHz) δ, ppm: 207.1, 115.0, 110.0, 102.6, 81.5, 76.9, 75.5, 65.2, 27.4, 26.9, 26.5, 25.5.
  • 28
  • [ 14686-88-5 ]
  • [ 14686-89-6 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose With palladium on activated charcoal; hydrogen In ethyl acetate for 3h; Stage #2: With methanol; sodium methylate at 20℃; for 0.5h; 2 Example 2 Compound I-1 (39.5g, 131.5mmol) was dissolved in ethyl acetate (100mL), Pd/C powder (2.0g) was added, and after stirring, it was placed in a hydrogen (40psi) atmosphere and stirred for 3 hours. TLC (PE: EA=1:1) The reaction is complete, the Pd/C powder is filtered off, and the filtrate is concentrated to obtain a pale yellow syrup intermediate (36.6g, 92%), The light yellow syrup obtained in the previous step was dissolved in methanol (100mL). Sodium methoxide was added to adjust the pH of the reaction solution to 8-10. Stir at room temperature for 30 minutes. TLC (PE:EA=1:1) showed that the reaction was complete. Add 732 H+ resin to adjust the reaction. The liquid is neutral, the resin is filtered off, the filtrate is concentrated, and the light yellow syrup I is separated by column chromatography (PE:EA=3:1), which solidifies (31.2g, 99%) after standing for a long time.
Multi-step reaction with 2 steps 1: 98 percent / H2 / Pd-C / ethyl acetate / 20 h / 20 °C / 1810.02 Torr 2: 99 percent / H2O; triethylamine / methanol / 3 h / 20 °C
Multi-step reaction with 2 steps 1: 90 percent / H2 / Pd / diethyl ether / 24 h 2: 91 percent / CH3ONa / methanol / 0.5 h / Ambient temperature
Multi-step reaction with 2 steps 1: 4.2 g / 5percent Pd/C, H2 / Ambient temperature 2: 2.5 g / Amberlite IRA-400 OH form / 40 h / Ambient temperature
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 120 h / 20 °C 2: sodium methylate / methanol / 3 h / 20 °C / pH 9.5
Multi-step reaction with 2 steps 1: hydrogen; 5%-palladium/activated carbon / ethanol / 6 h / 20 °C / 1034.32 Torr 2: sodium methylate / methanol / 0.5 h / 20 °C
Multi-step reaction with 2 steps 1: triethylsilane; palladium 10% on activated carbon; methanol / 20 - 35 °C / Large scale 2: sodium methylate / methanol / 1 h / 20 °C / pH 11

  • 29
  • [ 582-52-5 ]
  • [ 14686-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 97 percent / PDC; Ac2O / CH2Cl2 / 2 h / Heating 2: 90 percent / pyridine / 10 h / Heating 3: 98 percent / H2 / Pd-C / ethyl acetate / 20 h / 20 °C / 1810.02 Torr 4: 99 percent / H2O; triethylamine / methanol / 3 h / 20 °C
Multi-step reaction with 4 steps 1: PCC, molecular sieves / CH2Cl2 2: pyridine 3: H2 / Pd black / ethyl acetate 4: K2CO3 / methanol
Multi-step reaction with 2 steps 1: 86 percent / PDC, acetic anhydride / CH2Cl2 / 3 h / 78 °C 2: 1.) Ac2O, 2.) NaBH4 / 1.) pyridine, reflux, 2.) EtOH
  • 30
  • [ 14686-89-6 ]
  • [ 7508-81-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3
  • 31
  • [ 14686-89-6 ]
  • [ 214918-38-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH 12: 1H-tetrazole 13: m-CPBA 14: H2 / Pd/C 15: K2CO3 / methanol
  • 32
  • [ 14686-89-6 ]
  • ((3R,4S,5S,6R)-2,3,5-Trihydroxy-6-methyl-tetrahydro-pyran-4-yl)-carbamic acid benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl
  • 33
  • [ 14686-89-6 ]
  • [ 214918-32-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether
  • 34
  • [ 14686-89-6 ]
  • [ 37073-89-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C
  • 35
  • [ 14686-89-6 ]
  • [ 214918-31-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone
  • 36
  • [ 14686-89-6 ]
  • Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-amino-6-methyl-2-phosphonooxy-tetrahydro-pyran-3-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH 12: 1H-tetrazole 13: m-CPBA 14: H2 / Pd/C
  • 37
  • [ 14686-89-6 ]
  • Acetic acid (3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH
  • 38
  • [ 14686-89-6 ]
  • [ 451505-53-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine
  • 39
  • [ 14686-89-6 ]
  • [ 451505-46-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine
  • 40
  • [ 14686-89-6 ]
  • [ 214918-41-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 16 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH 12: 1H-tetrazole 13: m-CPBA 14: H2 / Pd/C 15: K2CO3 / methanol 16: a) Amberlite IR-120 resin (Et3NH+ form), b) 1H-tetrazole, pyridine
  • 41
  • [ 14686-89-6 ]
  • Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH 12: 1H-tetrazole
  • 42
  • [ 14686-89-6 ]
  • [ 214918-34-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH 12: 1H-tetrazole 13: m-CPBA
  • 43
  • [ 14686-89-6 ]
  • 3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether
Multi-step reaction with 4 steps 1: pyridine / CH2Cl2 / Ambient temperature 2: 2-methyl-propan-2-ol; tetrahydrofuran / 12 h / 80 °C 3: 95 percent / N-acetoxy-2-thiopyridone / CH2Cl2 / 0 - 5 °C / Irradiation 4: 87 percent / B(OH)3, H2O / ethanol / 8 h / 80 °C
  • 44
  • [ 582-52-5 ]
  • [ 14686-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: PCC / CH2Cl2 2: NaBH4 / ethanol
Multi-step reaction with 2 steps 1: PCC, 4A MS / CH2Cl2 / 3 h / Ambient temperature 2: NaBH4 / ethanol; H2O / 1 h / 0 °C
Multi-step reaction with 2 steps 1: pyridinium dichromate, Ac2O / CH2Cl2 / 2 h / 50 °C 2: NaBH4 / ethanol; H2O / 3 h / Ambient temperature
Multi-step reaction with 2 steps 1: 80 percent / PCC 2: 85 percent / NaBH4 / tetrahydrofuran
Multi-step reaction with 2 steps 1: RuO2, K2CO3, KIO4 / CH2Cl2 / 30 °C 2: 81 percent / NaBH4 / methanol
Multi-step reaction with 2 steps 1: 96 percent / pyridinium dichromate, Ac2O 2: 92 percent / NaBH4 / ethanol; H2O
Multi-step reaction with 2 steps 1: O2 / RuO4 2: NaBH4

  • 45
  • [ 14686-89-6 ]
  • [ 57099-04-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaH, nBu4NI / tetrahydrofuran / 0 - 25 °C 2: 90percent AcOH / H2O / 2.5 h / 40 °C
Multi-step reaction with 2 steps 1: 1.) NaH, 2.) Bu4I / 1.) THF, from 0 deg C to RT, 2.) THF, reflux, 1 h 2: aq. HCl / methanol / 12 h / Ambient temperature
Multi-step reaction with 2 steps 1: sodium hydride, tetrabutylammonium iodide 2: acetic acid / H2O
Multi-step reaction with 2 steps 1: NaH, Bu4NI / tetrahydrofuran / 2 h / Ambient temperature 2: 0.06 N HCl / methanol / 2 h / 55 °C
Multi-step reaction with 2 steps 1: NaH / dimethylformamide / 1.5 h / 25 °C 2: 80percent aq. AcOH / 24 h / 25 °C
Multi-step reaction with 2 steps 1: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, r.t., 45 min, 2) reflux, 1 h 2: conc. HCl / H2O; methanol / 23 h / Ambient temperature
Multi-step reaction with 2 steps 1: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) 25 deg C, 1.5 h 2: 2.85 g / aq. AcOH / 24 h / 25 °C

  • 46
  • [ 14686-89-6 ]
  • [ 4546-55-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: NaBH4 / methanol / 0.5 h / Ambient temperature 7: 68 percent / H2 / Pd black / ethanol / 9 h / 45 °C / 760 Torr
  • 47
  • [ 14686-89-6 ]
  • [ 184229-66-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C 7: 80 percent / Bu3SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C 8: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 9: 83 percent / H2 / Pd black / ethanol / 9 h / 45 °C / 760 Torr
  • 48
  • [ 14686-89-6 ]
  • [ 184229-59-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating
  • 49
  • [ 14686-89-6 ]
  • N-[9-((2R,3R,4S,5S)-4-Benzyloxy-5-formyl-3-hydroxy-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
  • 50
  • [ 14686-89-6 ]
  • [ 184229-68-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: NaBH4 / methanol / 0.5 h / Ambient temperature
  • 51
  • [ 14686-89-6 ]
  • [ 184229-65-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C 7: 80 percent / Bu3SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C 8: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature
  • 52
  • [ 14686-89-6 ]
  • [ 184229-61-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature
  • 53
  • [ 14686-89-6 ]
  • [ 184229-67-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C 7: 80 percent / Bu3SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C 8: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 9: 83 percent / H2 / Pd black / ethanol / 9 h / 45 °C / 760 Torr 10: 81 percent / pyridine / 1 h / 0 °C
  • 54
  • [ 14686-89-6 ]
  • [ 184229-64-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C 7: 80 percent / Bu3SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C
  • 55
  • [ 14686-89-6 ]
  • [ 184229-60-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C
  • 56
  • [ 14686-89-6 ]
  • [ 184229-62-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature
  • 57
  • [ 14686-89-6 ]
  • Diisopropyl-phosphoramidous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C 7: 80 percent / Bu3SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C 8: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 9: 83 percent / H2 / Pd black / ethanol / 9 h / 45 °C / 760 Torr 10: 81 percent / pyridine / 1 h / 0 °C 11: 77 percent / N,N-diisopropylethylamine / CH2Cl2 / 1 h / Ambient temperature
  • 58
  • [ 14686-89-6 ]
  • [ 184229-63-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C
  • 59
  • [ 14686-89-6 ]
  • (1R,3R,4R,5R)-3-<(1RS)-1-(ethoxycarbonyl)methyl-2-propenyl>-4-hydroxy-7,7-dimethyl-2,6,8-trioxabicyclo<3.3.0>octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C
Multi-step reaction with 3 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C
  • 60
  • [ 14686-89-6 ]
  • (1R,3R,4R,5R)-4-hydroxy-3-<(1R)-1-ethyl-3-hydroxypropyl>-7,7-dimethyl-2,6,8-trioxabicyclo<3.3.0>octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 48 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 6: 83 percent / H2 / Raney nickel T-4 / ethanol / 3 h
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 48 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 6: 83 percent / H2 / Raney nickel T-4 / ethanol / 3 h
Multi-step reaction with 7 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min 6: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 7: 83 percent / H2 / Raney nickel T-4 / ethanol / 3 h
  • 61
  • [ 14686-89-6 ]
  • (1R,3R,4R,5R)-4-hydroxy-3-<(1S)-1-ethyl-3-hydroxypropyl>-7,7-dimethyl-2,6,8-trioxabicyclo<3.3.0>octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 36 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 6: 91 percent / H2 / Raney nickel T-4 / ethanol / 3 h
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 36 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 6: 91 percent / H2 / Raney nickel T-4 / ethanol / 3 h
Multi-step reaction with 7 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min 6: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 7: 91 percent / H2 / Raney nickel T-4 / ethanol / 3 h
  • 62
  • [ 14686-89-6 ]
  • (1R,3R,4R,5R)-4-hydroxy-3-<(1S)-1-(2-hydroxyethyl)-2-propenyl>-7,7-dimethyl-2,6,8-trioxabicyclo<3.3.0>octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 48 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 48 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min 6: 92 percent / LiAlH4 / tetrahydrofuran / 1 h
  • 63
  • [ 14686-89-6 ]
  • (1R,3R,4R,5R)-4-hydroxy-3-<(1R)-1-(2-hydroxyethyl)-2-propenyl>-7,7-dimethyl-2,6,8-trioxabicyclo<3.3.0>octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 36 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 36 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min 6: 92 percent / LiAlH4 / tetrahydrofuran / 1 h
  • 64
  • [ 14686-89-6 ]
  • Benzoic acid (3aR,5R,6R,6aR)-5-((S)-1-ethoxycarbonylmethyl-allyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 48 percent / pyridine / 0.5 h
Multi-step reaction with 4 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 48 percent / pyridine / 0.5 h
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min
  • 65
  • [ 14686-89-6 ]
  • Benzoic acid (3aR,5R,6R,6aR)-5-((R)-1-ethoxycarbonylmethyl-allyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 36 percent / pyridine / 0.5 h
Multi-step reaction with 4 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 36 percent / pyridine / 0.5 h
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min
  • 66
  • [ 14686-89-6 ]
  • 5-acetamido-5-deoxy-1,2:7,8-di-O-isopropylidene-3-O-methylthiomethyl-β-L-threo-L-talooctofuranose-(1,4) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 62 percent / NaH / dioxane / Ambient temperature 2: 92 percent / 80percent aq. acetic acid / Ambient temperature 3: sodium periodate / H2O / 0.33 h 4: sodium borohydride / H2O / 0.33 h 5: 79 percent / pyridine / 12 h / Ambient temperature 6: 93.9 percent / NaI / butan-2-one / 2 h / Heating 7: 54.2 percent / phloroglucinol monohydrate, sodium nitrite / dimethylsulfoxide / 96 h / Ambient temperature 8: KF, tetrabutylammonium iodide / toluene / 2.5 h / Ambient temperature 9: H2 / Raney nickel T-4 / ethyl acetate; acetic acid / 20 h / 4045.3 Torr 10: 4.7 percent / methanol / 0.17 h / Ambient temperature
Multi-step reaction with 12 steps 1: 62 percent / NaH / dioxane / Ambient temperature 2: 92 percent / 80percent aq. acetic acid / Ambient temperature 3: sodium periodate / H2O / 0.33 h 4: sodium borohydride / H2O / 0.33 h 5: 79 percent / pyridine / 12 h / Ambient temperature 6: 93.9 percent / NaI / butan-2-one / 2 h / Heating 7: 54.2 percent / phloroglucinol monohydrate, sodium nitrite / dimethylsulfoxide / 96 h / Ambient temperature 8: KF, tetrabutylammonium iodide / toluene / 2.5 h / Ambient temperature 9: H2 / Raney nickel T-4 / ethyl acetate; acetic acid / 20 h / 4045.3 Torr 10: methanol / 0.17 h / Ambient temperature 11: 1.) phosphoric acid, DCC; 2.) oxalic acid / 1.) toluene, pyridine, DMSO, room temp., 3 h.; 2.) toluene, pyridine, DMSO, methanol, 30 min. 12: 29 percent / sodium borohydride / H2O; ethanol / 0.5 h / Ambient temperature
  • 67
  • [ 14686-89-6 ]
  • [ 13964-24-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: pyridine / CH2Cl2 / Ambient temperature 2: 2-methyl-propan-2-ol; tetrahydrofuran / 12 h / 80 °C 3: 95 percent / N-acetoxy-2-thiopyridone / CH2Cl2 / 0 - 5 °C / Irradiation 4: 87 percent / B(OH)3, H2O / ethanol / 8 h / 80 °C 5: 90 percent / pyridine / CH2Cl2 / Ambient temperature
  • 68
  • [ 14686-89-6 ]
  • [ 141903-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / Ambient temperature 2: 2-methyl-propan-2-ol; tetrahydrofuran / 12 h / 80 °C
  • 69
  • [ 14686-89-6 ]
  • [ 141903-85-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / CH2Cl2 / Ambient temperature 2: 2-methyl-propan-2-ol; tetrahydrofuran / 12 h / 80 °C 3: 95 percent / N-acetoxy-2-thiopyridone / CH2Cl2 / 0 - 5 °C / Irradiation
  • 70
  • [ 14686-89-6 ]
  • [ 84730-21-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 94 percent / pyridine / -10 - 0 °C 2: 59 percent / H2O, Dowex 50X 4-400 (H+) / methanol; dioxane / 72 h / 0 °C 3: 70 percent / LiN3, PPh3, CBr4 / dimethylformamide / 18 h / 0 deg C to room temperature 4: 1.) H2, 2.) NaOAc / 1.) 10percent Pd/C / 1.) EtOH, room temperature, 36 h, 2.) EtOH, reflux, 24 h 5: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, overnight
Multi-step reaction with 7 steps 1: 95 percent / pyridine 2: 74 percent / 0.8percent aq. H2SO4 / dioxane; methanol / 23 h / Ambient temperature 3: 94 percent / CBr4, PPh3 / tetrahydrofuran / 11 h / Ambient temperature 4: 96 percent / NaN3 / dimethylformamide / 8 h / 45 °C 5: H2 / Raney nickel / methanol / 24 h / Ambient temperature 6: NaOAc / ethanol / 15 h / Heating 7: Na2CO3 / acetone; H2O / 2 h / 0 °C
Multi-step reaction with 7 steps 1: 95 percent / pyridine 2: 74 percent / aq. H2SO4 3: Ph3P, CBr4 / tetrahydrofuran 4: NaN3 / dimethylformamide 5: hydrogen / Raney Ni 6: NaOAc / ethanol / Heating 7: Na2CO3 / acetone; H2O
  • 71
  • [ 14686-89-6 ]
  • [ 84730-20-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 94 percent / pyridine / -10 - 0 °C 2: 59 percent / H2O, Dowex 50X 4-400 (H+) / methanol; dioxane / 72 h / 0 °C 3: 70 percent / LiN3, PPh3, CBr4 / dimethylformamide / 18 h / 0 deg C to room temperature 4: 1.) H2, 2.) NaOAc / 1.) 10percent Pd/C / 1.) EtOH, room temperature, 36 h, 2.) EtOH, reflux, 24 h
Multi-step reaction with 6 steps 1: 95 percent / pyridine 2: 74 percent / 0.8percent aq. H2SO4 / dioxane; methanol / 23 h / Ambient temperature 3: 94 percent / CBr4, PPh3 / tetrahydrofuran / 11 h / Ambient temperature 4: 96 percent / NaN3 / dimethylformamide / 8 h / 45 °C 5: H2 / Raney nickel / methanol / 24 h / Ambient temperature 6: NaOAc / ethanol / 15 h / Heating
Multi-step reaction with 6 steps 1: 95 percent / pyridine 2: 74 percent / aq. H2SO4 3: Ph3P, CBr4 / tetrahydrofuran 4: NaN3 / dimethylformamide 5: hydrogen / Raney Ni 6: NaOAc / ethanol / Heating
  • 72
  • [ 14686-89-6 ]
  • [ 131603-35-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: NaH / dimethylformamide / 1.5 h / 25 °C 2: 80percent aq. AcOH / 24 h / 25 °C 3: pyridine / CH2Cl2 / 1 h / 2 °C 4: (COCl)2, DMSO, Et3N / CH2Cl2 / 1 h / -78 °C 5: 90 percent / KF / 18-crown-6 / dimethylformamide / 3 h / 25 °C 6: p-TsOH*H2O / 3 h / 25 °C 7: NaBH4 / aq. ethanol / 2 h / 25 °C 8: 82 percent / 80percent aq. AcOH / 15 h / 80 °C 9: Pb(OAc)4 / benzene / 0.67 h / 25 °C 10: KF / 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 11: Ac2O / p-TsOH*H2O / 1.5 h / 25 °C 12: 1.) 28percent aq. NH4OH / 2.) p-TsOH*H2O / 1.) 95percent aq. EtOH, 25 deg C, 2 h, 2.) 25 deg C, 2 h 13: 63 percent / n-Bu3SnH, AIBN / benzene / 3 h / 80 °C
Multi-step reaction with 13 steps 1: NaH / dimethylformamide / 1.5 h / 25 °C 2: 80percent aq. AcOH / 24 h / 25 °C 3: pyridine / CH2Cl2 / 1 h / 2 °C 4: (COCl)2, DMSO, Et3N / CH2Cl2 / 1 h / -78 °C 5: 90 percent / KF / 18-crown-6 / dimethylformamide / 3 h / 25 °C 6: p-TsOH*H2O / 3 h / 25 °C 7: NaBH4 / aq. ethanol / 2 h / 25 °C 8: 82 percent / 80percent aq. AcOH / 15 h / 80 °C 9: Pb(OAc)4 / benzene / 0.67 h / 25 °C 10: KF / 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 11: Ac2O / p-TsOH*H2O / 1.5 h / 25 °C 12: 1.) 28percent aq. NH4OH / 2.) p-TsOH*H2O / 1.) 95percent aq. EtOH, 25 deg C, 2 h, 2.) 25 deg C, 2 h 13: 62 percent / n-Bu3SnH, AIBN / benzene / 3 h / 80 °C
Multi-step reaction with 14 steps 1: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) 25 deg C, 1.5 h 2: 2.85 g / aq. AcOH / 24 h / 25 °C 3: pyridine / CH2Cl2 / 1 h / 2 °C 4: 770 mg / (COCl)2, DMSO / CH2Cl2 / 1 h / -78 °C 5: 90 percent / KF, 18-crown-6 / dimethylformamide / 3 h / 25 °C 6: p-TsOH*H2O / 3 h / 25 °C 7: NaBH4 / ethanol; H2O / 2 h / 25 °C 8: 82 percent / aq. AcOH / 15 h / 80 °C 9: Pb(OAc)4 / benzene / 0.67 h / 25 °C 10: KF, 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 11: 31 percent / Ac2O, p-TsOH*H2O / 1.5 h / 25 °C 12: aq. NH4OH / ethanol / 2 h / 25 °C 13: p-TsOH*H2O / 2 h / 25 °C 14: 63 percent / n-Bu3SnH, AIBN / benzene / 3 h / 80 °C
Multi-step reaction with 14 steps 1: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) 25 deg C, 1.5 h 2: 2.85 g / aq. AcOH / 24 h / 25 °C 3: pyridine / CH2Cl2 / 1 h / 2 °C 4: 770 mg / (COCl)2, DMSO / CH2Cl2 / 1 h / -78 °C 5: 90 percent / KF, 18-crown-6 / dimethylformamide / 3 h / 25 °C 6: p-TsOH*H2O / 3 h / 25 °C 7: NaBH4 / ethanol; H2O / 2 h / 25 °C 8: 82 percent / aq. AcOH / 15 h / 80 °C 9: Pb(OAc)4 / benzene / 0.67 h / 25 °C 10: KF, 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 11: 31 percent / Ac2O, p-TsOH*H2O / 1.5 h / 25 °C 12: aq. NH4OH / ethanol / 2 h / 25 °C 13: p-TsOH*H2O / 2 h / 25 °C 14: 62 percent / n-Bu3SnH, AIBN / benzene / 3 h / 80 °C

  • 73
  • [ 582-52-5 ]
  • [ 14686-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / 1 h / -78 °C 2: NaBH4 / aq. ethanol / 1.5 h / 2 °C
Multi-step reaction with 2 steps 1: pyridinium chlorochromate, molecular sieve / CH2Cl2 2: NaBH4 / ethanol
Multi-step reaction with 2 steps 1: PCC, mol. sieves / CH2Cl2 2: NaBH4 / ethanol
Multi-step reaction with 2 steps 1: Ru2O, NaIO4 2: NaBH4

  • 74
  • [ 14686-89-6 ]
  • [ 78785-21-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h
Multi-step reaction with 11 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h
  • 75
  • [ 14686-89-6 ]
  • [ 80890-30-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C 13: Amberlite IR-120 / H2O / 8 h / 90 °C
Multi-step reaction with 13 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C 13: Amberlite IR-120 / H2O / 8 h / 90 °C
  • 76
  • [ 14686-89-6 ]
  • (3aR,5R,6S,6aR)-5-(2-Benzyloxy-ethyl)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C
Multi-step reaction with 12 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C
  • 77
  • [ 14686-89-6 ]
  • [ 81114-61-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 60 percent / tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: H2 / Pd-C / ethanol / 0.5 h / 25 °C
  • 78
  • [ 14686-89-6 ]
  • [ 78822-30-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C
Multi-step reaction with 10 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C
  • 79
  • [ 14686-89-6 ]
  • [ 80879-41-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 60 percent / tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: H2 / Pd-C / ethanol / 0.5 h / 25 °C 10: KH / tetrahydrofuran / 6 h / 60 °C 11: 98 percent / Amberlite IR-120 / H2O / 8 h / 90 °C
  • 80
  • [ 14686-89-6 ]
  • [ 80879-42-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 60 percent / tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: H2 / Pd-C / ethanol / 0.5 h / 25 °C 10: KH / tetrahydrofuran / 6 h / 60 °C 11: 98 percent / Amberlite IR-120 / H2O / 8 h / 90 °C 12: 1.) NaBH4, 2.) NaIO4 / 1.) EtOH, 25 deg C, 48 h, 2.) EtOH-H2O, 0 deg C
  • 81
  • [ 14686-89-6 ]
  • [ 80879-40-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 60 percent / tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: H2 / Pd-C / ethanol / 0.5 h / 25 °C 10: KH / tetrahydrofuran / 6 h / 60 °C
  • 82
  • [ 14686-89-6 ]
  • Methanesulfonic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C
Multi-step reaction with 9 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C
  • 83
  • [ 14686-89-6 ]
  • [ 80890-17-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 60 percent / tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: H2 / Pd-C / ethanol / 0.5 h / 25 °C 10: KH / tetrahydrofuran / 6 h / 60 °C 11: 98 percent / Amberlite IR-120 / H2O / 8 h / 90 °C 12: 1.) NaBH4, 2.) NaIO4 / 1.) EtOH, 25 deg C, 48 h, 2.) EtOH-H2O, 0 deg C 13: 87 percent / toluene / 3 h / 60 °C
  • 84
  • [ 14686-89-6 ]
  • (E)-(4S,5S,6R)-8-Benzyloxy-4,6-dihydroxy-5-methyl-oct-2-enoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C 13: Amberlite IR-120 / H2O / 8 h / 90 °C 14: toluene / 48 h / 25 °C
Multi-step reaction with 14 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C 13: Amberlite IR-120 / H2O / 8 h / 90 °C 14: toluene / 48 h / 25 °C
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