Reaction #6105

ord-0ca6092933ea4a7da1ca782d6487ff3a

Reaction equation

Sc1ccccc1
benzenethiol
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-xylopyranosyl bromide
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2)SC[C@H]1OC(C)=O
expected product
Yield 52.3%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2)SC[C@H]1OC(C)=O
phenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Yield 52.3%

Reactants

Sc1ccccc1
benzenethiol
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-xylopyranosyl bromide
—
mercuric cyanide

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 4 g (36.3.10-3 mol) of benzenethiol, 14 g (39.4.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-xylopyranosyl bromide and 10 g (39.10-3 mol) of mercuric cyanide (Hg(CN)2), 7.3 g of the expected product are obtained after crystallization from ether.

Source

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