Thiophenol → phenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 6009

Reaction equation

HRID 6009 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([O:11][C@@H:12]1[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([O:22][C:23](=[O:25])[CH3:24])[CH2:15][S:14][C@@H:13]1Br)(=[O:10])[CH3:9]>>[C:8]([O:11][C@@H:12]1[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([O:22][C:23](=[O:25])[CH3:24])[CH2:15][S:14][C@H:13]1[S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:10])[CH3:9]

Participants

3

Reactant 2

HCID 7969ThiophenolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Product 1

HCID 14795349phenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideYield 52.3%

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.

Workup

  1. customIf the procedure described in Preparation I

Sources & evidence

ORD record
ord-0ca6092933ea4a7da1ca782d6487ff3a
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Linked notes

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