Reaktion #6138

ord-77ee1249bab045feb3c459539c7d4d4c

Reaktionsgleichung

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C#N
2-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
C[O-].[Na+]
sodium methylate
→
N#Cc1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O
expected product
Ausbeute 88.0%
N#Cc1ccccc1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O
2-cyanophenyl 5-thio-β-D-xylopyranoside
Ausbeute 88.0%

Edukte

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C#N
2-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
—
solution
C[O-].[Na+]
sodium methylate

Reagenzien

Keine

Lösungsmittel

CO
methanol
CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeIf the procedure described in Preparation LXXXIV

Vorschrift

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.

Quelle

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