Reaction #6101

ord-9b0f85be4c6140d5896fab7059cbf008

Reaction equation

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide
N#Cc1ccccc1S
2-mercaptobenzonitrile
N#[C][Hg][C]#N
Hg(CN)2
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C#N)SC[C@H]1OC(C)=O
expected product
Yield 50.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C#N)SC[C@H]1OC(C)=O
2-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Yield 50.0%

Reactants

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide
N#Cc1ccccc1S
2-mercaptobenzonitrile
—
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherIf the procedure described in Preparation I

Procedure

If the procedure described in Preparation I is followed starting from 9.70 g (72.10-3 mol) of 2-mercaptobenzonitrile, 19.45 g (77.10-3 mol) of mercuric cyanide, Hg(CN)2, and 27.4 g (77.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 14.7 g (yield: 50%) of the expected product are obtained.

Source

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