3,6-anhydro-5-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol | 1092944-29-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-anhydro-5-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol
• 英文别名: (2R,3R,4S,5R)-2-ethenyl-5-(hydroxymethyl)-4-phenylmethoxyoxolan-3-ol
• CAS: 1092944-29-0
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: BQUZCCMKCFBGEW-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3S,4R,5S,6R)-3,5-dibenzyloxy-4,7-dihydroxy-6-(4-methoxybenzyl)oxyhept-1-ene 在 2,2'-联苯二甲酸 、 diphenylammonium triflate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以79%的产率得到3,6-anhydro-5-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol
  参考文献：
  名称：

  Highly stereoselective synthesis of C-vinyl furanosides through acid-catalyzed SN2 inversion at the C-3 position of 1,2-dideoxy-hept-1-enitols

  摘要：

  A highly stereoselective synthesis of C-vinyl furamosides through the S(N)2 inversion at the C-3 position of the 1,2-dideoxy-hept-1-enitols is disclosed. Treatment of the 1,2-dideoxy-hept-1-enitols with diphenylammonium trifluoromethanesulfonate as the acid catalyst produced the C-vinyl furanosides (3,6-anhydro-1,2-dideoxy-hept-1-enitol derivatives) via a subsequent S(N)2 intramolecular debenzyloxyationcycloetherification reaction at the C-3 position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.08.017

文献信息

• Highly stereoselective synthesis of C-vinyl furanosides through acid-catalyzed SN2 inversion at the C-3 position of 1,2-dideoxy-hept-1-enitols
  作者：Hitoshi Tsuchiya、Noriaki Asakura、Yasunori Ikeda、Hidetoshi Yamada

  DOI：10.1016/j.carres.2008.08.017

  日期：2008.11

  A highly stereoselective synthesis of C-vinyl furamosides through the S(N)2 inversion at the C-3 position of the 1,2-dideoxy-hept-1-enitols is disclosed. Treatment of the 1,2-dideoxy-hept-1-enitols with diphenylammonium trifluoromethanesulfonate as the acid catalyst produced the C-vinyl furanosides (3,6-anhydro-1,2-dideoxy-hept-1-enitol derivatives) via a subsequent S(N)2 intramolecular debenzyloxyationcycloetherification reaction at the C-3 position. (C) 2008 Elsevier Ltd. All rights reserved.