Reaction #6098

ord-e160f17724b945938456d36adf413951

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#Cc1cccc(S)c1
3-mercaptobenzonitrile
N#[C][Hg][C]#N
Hg(CN)2
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc(C#N)c2)SC[C@H]1OC(C)=O
expected product
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc(C#N)c2)SC[C@H]1OC(C)=O
3-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside

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#Cc1cccc(S)c1
3-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 9.3 g (67.10-3 mol) of 3-mercaptobenzonitrile, 18 g (73.10-3 mol) of mercuric cyanide, Hg(CN)2, and 26.14 g (73.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 8.55 g of the expected product are obtained.

Source

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