Reaction #6143

ord-3dad95ee87aa442ca66bdccf28072882

Reaction equation

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1[N+](=O)[O-]
2-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
C[O-].[Na+]
sodium methylate
→
O=[N+]([O-])c1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O
expected product
Yield 68.0%
O=[N+]([O-])c1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O
2-nitrophenyl 5-thio-β-D-xylopyranoside
Yield 68.0%

Reactants

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1[N+](=O)[O-]
2-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
—
solution
C[O-].[Na+]
sodium methylate

Reagents

None

Solvents

CO
methanol
CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherIf the procedure described in Preparation LXXXIV

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246961uspto-grants-1993_09