HCID 10886810, compound → 3,5-di-O-benzyl-2-deoxy-L-threo-pentose dibenzyl dithioacetal

HRID 1707949Notes

Reaction equation

HRID 1707949 reaction equation
[CH2:1]([S:8][CH:9]([S:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:10][C@@H:11]([C@H:20]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:21]C(=O)C1C=CC=CC=1)[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].CCCCCC.C(OCC)(=O)C>ClCCl.CO>[CH2:40]([S:39][CH:9]([S:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][C@@H:11]([C@H:20]([CH2:30][O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[OH:21])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 3

HCID 10886810HCID 10886810, compoundHCID 10942334Sodium MethoxideHCID 21226206Ethyl acetate hexane

Product 1

HCID 150599573,5-di-O-benzyl-2-deoxy-L-threo-pentose dibenzyl dithioacetal

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-O-benzoyl-3,5-di-O-benzyl-2-deoxy-L-threo-pentose dibenzyl dithioacetal (88.8 g, 137 mmol) in dichloromethane (500 ml) was added a solution of sodium methoxide (11.1 g, 206 mmol) in methanol (205 ml) dropwise, with stirring, at 0° C. The reaction mixture was then allowed to warm to room temperature over a period of 3 hours. At the end of this time TLC (hexane-ethyl acetate [4:1]) revealed complete conversion to a slower moving component (Rf 0.31). The mixture was then poured into a 5% solution of NaH2PO4 and extracted with dichloromethane. The dichloromethane extracts were then washed with a 5% solution of sodium hydrogen carbonate and water, dried (magnesium sulphate) and evaporated. The crude title product was applied to a silica gel column eluted with hexane-ethyl acetate (4:1). Combination of the appropriate fractions gave the title product as a clear colourless syrup.

Workup

  1. temperatureto warm to room temperature over a period of 3 hours
  2. extractionextracted with dichloromethane
  3. washThe dichloromethane extracts were then washed with a 5% solution of sodium hydrogen carbonate and water
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. washeluted with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-59f9c9fc71294a27828e4a3a45e757a1
Source dataset
uspto-grants-1994_10
Patent number
US05356882

Reaction notes

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