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

HRID 6016Notes

Reaction equation

HRID 6016 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:16]([O:19][C@@H:20]1[C@@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:24]([O:30][C:31](=[O:33])[CH3:32])[CH2:23][S:22][C@@H:21]1Br)(=[O:18])[CH3:17].[Hg](C#N)C#N>>[C:16]([O:19][C@@H:20]1[C@@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:24]([O:30][C:31](=[O:33])[CH3:32])[CH2:23][S:22][C@H:21]1[S:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 11591Mercuric cyanideHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromideHCID 147953354'-Mercaptobiphenyl-4-carbonitrile

Product 1

HCID 147953594-(4-cyanophenyl)phenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideYield 10.2%

Procedure

If the procedure described in Preparation I is followed starting from 2.3 g (10.9.10-3 mol) of 4-(4-mercaptophenyl)benzonitrile, 4.26 g (11.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 2.75 g (10.9.10-3 mol) of mercuric cyanide (Hg(CN)2), 0.540 g (yield: 10%) of the expected product is obtained after purification by flash chromatography using methylene chloride as the eluent.

Workup

  1. customIf the procedure described in Preparation I

Sources & evidence

ORD record
ord-5695140c336e4ddc99bfce8ba1baa852
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Reaction notes

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