Reaction #6110

ord-b4d8de5548014418855293f67040f611

Reaction equation

FC(F)(F)c1ccccc1S
2trifluoromethylbenzenethiol
N#[C][Hg][C]#N
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2
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
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C(F)(F)F)SC[C@H]1OC(C)=O
expected product
Yield 34.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C(F)(F)F)SC[C@H]1OC(C)=O
2-trifluoromethylphenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Yield 34.0%

Reactants

FC(F)(F)c1ccccc1S
2trifluoromethylbenzenethiol
N#[C][Hg][C]#N
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2
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

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 1.8 g (10.10-3 mol) of 2trifluoromethylbenzenethiol, 2.55 g (10.10-3 mol) of mercuric cyanide (Hg(CN)2) and 3.95 g (11.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1.53 g (yield: 34%) of the expected product are obtained.

Source

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