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

HRID 907058Notes

Reaction equation

HRID 907058 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.[C:16]([O:19][C@@H:20]1[C@@H:34]([O:35][C:36](=[O:38])[CH3:37])[C@H:33]([O:39][C:40](=[O:42])[CH3:41])[CH2:32][S:31][C@H:21]1[O:22][C:23]1[CH:28]=[C:27](Br)[CH:26]=[CH:25][C:24]=1[Cl:30])(=[O:18])[CH3:17]>>[C:16]([O:19][C@@H:20]1[C@@H:34]([O:35][C:36](=[O:38])[CH3:37])[C@H:33]([O:39][C:40](=[O:42])[CH3:41])[CH2:32][S:31][C@H:21]1[O:22][C:23]1[CH:28]=[C:27]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)[CH:26]=[CH:25][C:24]=1[Cl:30])(=[O:18])[CH3:17]

Participants

3

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 673956335-bromo-2-chlorophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 673964622-Chloro-5-(1-methyl-1H-pyrazol-4-yl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Procedure

By carrying out the operation analogously to example 87, starting from 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-2-chlorophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained according to preparation X, the expected product is obtained and is reacted further without additional purification in order to obtain the nonacetylated xyloside.

Workup

  1. customobtained
  2. customaccording to preparation X

Sources & evidence

ORD record
ord-f7a6a329011040c19996ff92442bedf5
Source dataset
uspto-grants-2011_09
Patent number
US08013010B2

Reaction notes

Loading…