2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosylamine | 905832-58-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosylamine
• CAS: 905832-58-8
• 化学式: C₂₇H₂₉NO₅
• 分子量: 447.531
• InChiKey: ZZIRJOJRVSWFRP-ABKQVJMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosylamine 、 2,2'-双溴双苯 在 racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl 、 tris(dibenzylideneacetone)dipalladium (0) 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以33%的产率得到2,3-di-O-benzyl-4,6-O-benzilidene-β-D-glucopiranosylcarbazole
  参考文献：
  名称：

  One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

  摘要：

  The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2'-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.087
• 作为产物：
  描述：

  4,6-O-benzylidene-β-D-glucopyranosyl azide 在 Lindlar's catalyst 氢气 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosylamine
  参考文献：
  名称：

  One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

  摘要：

  The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2'-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.087