ethyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside | 439684-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-azido-6-ethylsulfanyl-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 439684-08-9
• 化学式: C₂₉H₃₁N₃O₅S
• 分子量: 533.648
• InChiKey: ZIOUJZZFOUEGHR-ROJUMVHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 在 溴 、 1,4,7,10,13,16-Hexaoxacyclononadecane (19-crown-6) 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.17h， 生成 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranosyl thiocyanate
  参考文献：
  名称：

  Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances

  摘要：

  Short synthetic routes to protected derivatives of 2-amino-2-deoxy-alpha-D-glucopyranosyl-(1-->6)-D-myo-inositol are described. Various 2-azido-2-deoxy-glucosyl donors were synthesized, starting front, D-Glucal or glucosamine hydrochloride. Derivatives of 1,2- and 2,3-D-myo-inositol-camphanylidene acetals were prepared to function as glycosyl acceptors. The subsequent glycosylations produced useful building blocks for the synthesis of GPI-anchor substances. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01241-8
• 作为产物：
  描述：

  ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 triflic azide 、 sodium cyanoborohydride 、 乙二胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 正丁醇 为溶剂， 反应 30.5h， 生成 ethyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances

  摘要：

  Short synthetic routes to protected derivatives of 2-amino-2-deoxy-alpha-D-glucopyranosyl-(1-->6)-D-myo-inositol are described. Various 2-azido-2-deoxy-glucosyl donors were synthesized, starting front, D-Glucal or glucosamine hydrochloride. Derivatives of 1,2- and 2,3-D-myo-inositol-camphanylidene acetals were prepared to function as glycosyl acceptors. The subsequent glycosylations produced useful building blocks for the synthesis of GPI-anchor substances. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01241-8