4-(Trifluoromethyl)thiophenol → 4-trifluoromethylphenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 6000

Reaction equation

HRID 6000 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.[C:12]([O:15][C@@H:16]1[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:19][S:18][C@@H:17]1Br)(=[O:14])[CH3:13]>[O-2].[Zn+2]>[C:12]([O:15][C@@H:16]1[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:19][S:18][C@H:17]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:14])[CH3:13]

Participants

4

Reactant 2

HCID 1366534-(Trifluoromethyl)thiophenolHCID 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 48%

Reagents, catalysts & solvents 1

HCID 3007857Zinc OxideCatalyst

Procedure

If the procedure described in Preparation IV is followed starting from 5.6 g (32.10-3 mol) of 4trifluoromethylbenzenethiol, 12.3 g (35.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 2.55 g (32.10-3 mol) of zinc oxide (ZnO), 7.4 g (yield: 48%) of the expected product are obtained after precipitation in ether.

Sources & evidence

ORD record
ord-6e968d420acc44f5a9c97e2954212c9c
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Linked notes

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