Thiophene-3-boronic acid → 3-(3-Thienyl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 907060Notes

Reaction equation

HRID 907060 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].[S:27]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28]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:29]2[CH:30]=[CH:31][S:27][CH:28]=2)[CH:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 673956003-bromophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 673970803-(3-Thienyl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideYield 26%

Procedure

By carrying out the operation analogously to example 13, starting from 3-bromophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation VII, and 3-thiopheneboronic acid, the expected product is obtained in the form of white crystals with a yield of 26%.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-afb30c41cfdb4288a658d4366e1ca85e
Source dataset
uspto-grants-2011_09
Patent number
US08013010B2

Reaction notes

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