1,3,5-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 3-(1,3,5-Trimethyl-1H-pyrazol-4-yl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 907057Notes

Reaction equation

HRID 907057 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].CC1(C)C(C)(C)OB([C:35]2[C:36]([CH3:42])=[N:37][N:38]([CH3:41])[C:39]=2[CH3:40])O1>>[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:35]2[C:36]([CH3:42])=[N:37][N:38]([CH3:41])[C:39]=2[CH3:40])[CH:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 27953111,3,5-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 673956003-bromophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 673979533-(1,3,5-Trimethyl-1H-pyrazol-4-yl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideYield 46%

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 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,5-trimethyl-1H-pyrazole, the expected product is obtained in the form of a white solid with a yield of 46%.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-6ecfa38c84594867bc2996805b29520c
Source dataset
uspto-grants-2011_09
Patent number
US08013010B2

Reaction notes

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