2-azido-3,4,6-tri-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-D-galactitol | 1132966-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-azido-3,4,6-tri-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-D-galactitol
• 英文别名: (2R,3S,4R,5S)-5-azido-6-[tert-butyl(dimethyl)silyl]oxy-1,3,4-tris(phenylmethoxy)hexan-2-ol
• CAS: 1132966-65-4
• 化学式: C₃₃H₄₅N₃O₅Si
• 分子量: 591.823
• InChiKey: BUKRYSOLUFXYDW-BVEPWEIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.44
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-azido-3,4,6-tri-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-D-galactitol 、 2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到2-azido-5-O-[2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl]-3,4,6-tri-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-D-galactitol
  参考文献：
  名称：

  Synthesis of a unique trisaccharide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus

  摘要：

  The first stereoselective synthesis of a unique trisaccharide containing an open-chain glycosyl cyclic acetal moiety found in the cell wall of Proteus has been successfully achieved. Most of the intermediate steps are high yielding and highly reproducible. The acetal linkage of the open-chain D-galactosamine moiety with an (S)-configuration was formed exclusively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.006
• 作为产物：
  描述：

  (2S,3R,4S,5R)-2-azido-3,4,6-tris(benzyloxy)hexane-1,5-diol 、 叔丁基二甲基氯硅烷 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以90%的产率得到2-azido-3,4,6-tri-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-D-galactitol
  参考文献：
  名称：

  Synthesis of a unique trisaccharide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus

  摘要：

  The first stereoselective synthesis of a unique trisaccharide containing an open-chain glycosyl cyclic acetal moiety found in the cell wall of Proteus has been successfully achieved. Most of the intermediate steps are high yielding and highly reproducible. The acetal linkage of the open-chain D-galactosamine moiety with an (S)-configuration was formed exclusively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.006

文献信息

• Synthesis of a unique trisaccharide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus
  作者：Chinmoy Mukherjee、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2008.12.006

  日期：2008.12

  The first stereoselective synthesis of a unique trisaccharide containing an open-chain glycosyl cyclic acetal moiety found in the cell wall of Proteus has been successfully achieved. Most of the intermediate steps are high yielding and highly reproducible. The acetal linkage of the open-chain D-galactosamine moiety with an (S)-configuration was formed exclusively. (C) 2008 Elsevier Ltd. All rights reserved.