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

HRID 6042Notes

Reaction equation

HRID 6042 reaction equation
C([O:4][C@@H:5]1[C@@H:19]([O:20]C(=O)C)[C@H:18]([O:24]C(=O)C)[CH2:17][S:16][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]#[N: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]#[N:15])[C@@H:6]1[S:16][CH2:17][C@@H:18]([OH:24])[C@H:19]([OH:20])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 150678542-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 150678552-cyanophenyl 5-thio-beta-D-xylopyranosideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

If the procedure described in Preparation LXXXIV is followed starting from 1.26 g (3.2.10-3 mol) of 2-cyanophenyl 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 70 ml of methanol for 30 min, 0.75 g (yield: 88%) of the expected product is obtained after precipitation in ether and lyophilization.

Workup

  1. customIf the procedure described in Preparation LXXXIV

Sources & evidence

ORD record
ord-77ee1249bab045feb3c459539c7d4d4c
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Reaction notes

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