Mercuric cyanide → 4-trifluoromethylphenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 5999

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.[Hg](C#N)C#N.[C:17]([O:20][C@@H:21]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:25]([O:31][C:32](=[O:34])[CH3:33])[CH2:24][S:23][C@@H:22]1Br)(=[O:19])[CH3:18]>>[C:17]([O:20][C@@H:21]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:25]([O:31][C:32](=[O:34])[CH3:33])[CH2:24][S:23][C@H:22]1[S:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:10])[F:11])=[CH:8][CH:7]=1)(=[O:19])[CH3:18]

Participants

Reactant 3

HCID 11591Mercuric cyanide

HCID 1366534-(Trifluoromethyl)thiophenol

HCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Product 1

HCID 147953414-trifluoromethylphenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideYield 40%

Procedure

If the procedure described in Preparation I is followed starting from 5.58 g (32.10-3 mol) of 4-tri-fluoromethylbenzenethiol, 8.87 g (35.10-3 mol) of mercuric cyanide, Hg(CN)2, and 12.3 g (35.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 6.2 g (yield: 40%) of the expected product are obtained.

Workup

customIf the procedure described in Preparation I

Sources & evidence

ORD record: ord-0e5f513459a84d2786a08726e0e9d65d
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246961

Linked notes

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