Sodium Methoxide → 3-acetylphenyl 5-thio-beta-D-xylopyranoside

HRID 2373004Notes

Reaction equation

HRID 2373004 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]=[C:10]([C:14](=[O:16])[CH3:15])[CH:9]=1)(=O)C.C[O-].[Na+]>CO>[O:7]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:16])[CH3:15])[CH:9]=1)[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 150678523-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 150678533-acetylphenyl 5-thio-beta-D-xylopyranosideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

If the procedure described in Preparation LXXXIV is followed starting from 1.36 g (3.3.10-3 mol) of 3-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 0.2 ml of a solution of sodium methylate in methanol (8% w/v of Na), reacted in 50 ml of methanol for 30 min, 0.8 g (yield: 85%) of the expected product is obtained after crystallization from an ethanol/ether mixture.

Workup

  1. customIf the procedure described in Preparation LXXXIV

Sources & evidence

ORD record
ord-9acffb50a7cb42739a52dadbeba1f008
Source dataset
uspto-grants-1992_03
Patent number
US05101048

Reaction notes

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