Mercuric cyanide → 3,5-bis(trifluoromethyl)phenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 6018Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([SH:13])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Hg](C#N)C#N.[C:21]([O:24][C@@H:25]1[C@@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:29]([O:35][C:36](=[O:38])[CH3:37])[CH2:28][S:27][C@@H:26]1Br)(=[O:23])[CH3:22]>>[C:21]([O:24][C@@H:25]1[C@@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:29]([O:35][C:36](=[O:38])[CH3:37])[CH2:28][S:27][C@H:26]1[S:13][C:5]1[CH:4]=[C:3]([C:2]([F:14])([F:1])[F:15])[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=1)(=[O:23])[CH3:22]

Participants

Reactant 3

HCID 11591Mercuric cyanide2×

HCID 5186903,5-Bis(trifluoromethyl)benzenethiol

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

Product 1

HCID 147953613,5-bis(trifluoromethyl)phenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideYield 35.7%

Procedure

If the procedure described in Preparation I is followed starting from 1.6 g (6.5.10-3 mol) of 3,5-bis(trifluoromethyl)benzenethiol, 1.64 g (6.5.10-3 mol) of mercuric cyanide, Hg(CN)2, and 2.54 g (7.5.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1.2 g (yield: 35.7%) of the expected product are obtained. M.p.=201° C.

Workup

customIf the procedure described in Preparation I

Sources & evidence

ORD record: ord-21012e4031214f1599ceb78ee6f4b6dc
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246961

Reaction notes

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