ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside | 439684-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-O-acetyl-2-azido-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] acetate
• CAS: 439684-07-8
• 化学式: C₂₄H₂₉N₃O₅S
• 分子量: 471.577
• InChiKey: NXAYUETVZWKYTD-RMRNXIRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 Acetic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran-3-yl ester
  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 30.17h， 生成 ethyl 4-O-acetyl-2-azido-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

文献信息

• Solid-Phase and Solution-Phase Synthesis of Glycosylphosphatidylinositol Glycans
  申请人：Seeberger Peter H.

  公开号：US20120003260A1

  公开（公告）日：2012-01-05

  One aspect of the present invention relates to solution-phase approaches to GPI synthesis. Another aspect of the present invention relates to key building blocks, and syntheses thereof, useful for GPI assembly. Yet another aspect of the invention relates to an automated method for the synthesis of GPIs and fragments thereof.