2-Methoxypyrimidine-5-boronic acid → 3-(2-Methoxy-5-pyrimidinyl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 907068Notes

Reaction equation

HRID 907068 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:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=1)(=[O:3])[CH3:2].[CH3:27][O:28][C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][N:30]=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:13]=[CH:12][CH:11]=[C:10]([C:32]2[CH:31]=[N:30][C:29]([O:28][CH3:27])=[N:34][CH:33]=2)[CH:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 673956003-bromophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 673963313-(2-Methoxy-5-pyrimidinyl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Procedure

By carrying out the operation analogously to example 3, starting from 3-bromophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation VII, and 2-methoxy-5-pyrimidineboronic 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-1091b088e0da4b7baad7e666136a6d64
Source dataset
uspto-grants-2011_09
Patent number
US08013010B2

Reaction notes

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