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

HRID 2373011Notes

Reaction equation

HRID 2373011 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[N+:14]([O-:16])=[O:15])(=O)C.C[O-].[Na+]>CO>[O:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O: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 150678582-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 150678592-nitrophenyl 5-thio-beta-D-xylopyranosideYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

If the procedure described in Preparation LXXXIV is followed starting from 0.85 g (2.05.10-3 mol) of 2-nitrophenyl 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, 0.4 g (yield: 68%) 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-5165e3cc19604c929018e5537499a432
Source dataset
uspto-grants-1992_03
Patent number
US05101048

Reaction notes

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