2-Methylpyridine-5-boronic acid → 6-(6-Methyl-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

HRID 419803Notes

Reaction equation

HRID 419803 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][C:11](Br)=[CH:12][CH:13]=1)(=[O:3])[CH3:2].[CH3:27][C:28]1[N:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1>>[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][C:11]([C:31]2[CH:32]=[N:33][C:28]([CH3:27])=[CH:29][CH:30]=2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 27630812-Methylpyridine-5-boronic acidHCID 866250296-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 666510546-(6-Methyl-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

Procedure

By carrying out the operation analogously to example 1, starting from 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation IV, and 6-methyl-3-pyridineboronic acid, the desired product is obtained in the form of a white solid (yield=62%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-fb84a147ae4a4adbb44ed7b8c4498505
Source dataset
uspto-grants-2012_01
Patent number
US08093394B2

Reaction notes

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