Sodium Methoxide → 2-acetylphenyl 5-thio-beta-D-xylopyranoside

HRID 6049Notes

Reaction equation

HRID 6049 reaction equation
C([O:4][C@@H:5]1[C@@H:20]([O:21]C(=O)C)[C@H:19]([O:25]C(=O)C)[CH2:18][S:17][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:16])[CH3:15])(=O)C.C[O-].[Na+]>CO>[O:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:16])[CH3:15])[C@@H:6]1[S:17][CH2:18][C@@H:19]([OH:25])[C@H:20]([OH:21])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 150678602-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 150678612-acetylphenyl 5-thio-beta-D-xylopyranosideYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

If the procedure described in Preparation LXXXIV is followed starting from 0.88 g (2.1.10-3 mol) of 2-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 0.1 ml of a solution of sodium methylate in methanol (8% w/v of Na), reacted in 50 ml of methanol for 30 min, 0.51 g (yield: 84%) of the expected product is obtained after purification by chromatography on silica gel using a chloroform/methanol mixture (12/1 v/v) as the eluent, and lyophilization.

Workup

  1. customIf the procedure described in Preparation LXXXIV

Sources & evidence

ORD record
ord-10114c1b82204ff0a3cd5529f1b818ad
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Reaction notes

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