4-Nitrobenzenethiol → 4-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 5997

Reaction equation

HRID 5997 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]([O:14][C@@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:18][S:17][C@@H:16]1Br)(=[O:13])[CH3:12]>[O-2].[Zn+2]>[C:11]([O:14][C@@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:18][S:17][C@H:16]1[S:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 158094-NitrobenzenethiolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Product 1

HCID 106462404-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideYield 79%

Reagents, catalysts & solvents 1

HCID 3007857Zinc OxideCatalyst

Procedure

If the procedure described in Preparation IV is followed starting from 6 g (38.10-3 mol) of 4-nitrobenzenethiol, 15.1 g (42.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 3.2 g (39.10-3 mol) of zinc oxide (ZnO), 13 g (yield: 79%) of the expected product are obtained after precipitation in ether.

Sources & evidence

ORD record
ord-62639ba3ea8e47aa90d2c7105c41edd9
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Linked notes

Loading…