2-Methylpyridine-4-boronic acid → 2-Chloro-5-(2-methyl-4-pyridinyl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 907065Notes

Reaction equation

HRID 907065 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][S:16][C@H:6]1[O:7][C:8]1[CH:13]=[C:12](Br)[CH:11]=[CH:10][C:9]=1[Cl:15])(=[O:3])[CH3:2].[CH3:28][C:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[CH:31][N:30]=1>>[C:1]([O:4][C@@H:5]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][S:16][C@H:6]1[O:7][C:8]1[CH:13]=[C:12]([C:33]2[CH:32]=[CH:31][N:30]=[C:29]([CH3:28])[CH:34]=2)[CH:11]=[CH:10][C:9]=1[Cl:15])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 41926642-Methylpyridine-4-boronic acidHCID 673956335-bromo-2-chlorophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 673966032-Chloro-5-(2-methyl-4-pyridinyl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Procedure

By carrying out the operation analogously to example 3, starting from 5-bromo-2-chlorophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation X, and 2-methyl-4-pyridineboronic acid, the expected product is obtained and is reacted further without additional purification in order to obtain the nonacetylated xyloside.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-11394fffa15043b5a738fdf9814aef7c
Source dataset
uspto-grants-2011_09
Patent number
US08013010B2

Reaction notes

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