(1R,2R,3S,10aS)-decahydropyrido[1,2-a]azepine-1,2,3-triol | 1228764-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (1R,2R,3S,10aS)-decahydropyrido[1,2-a]azepine-1,2,3-triol
• 英文别名: (1R,2R,3S,10aS)-1,2,3,4,6,7,8,9,10,10a-decahydropyrido[1,2-a]azepine-1,2,3-triol
• CAS: 1228764-22-4
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: UVUKYBLHTPWZLH-AXTSPUMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,10aS)-decahydropyrido[1,2-a]azepine-1,2,3-triol 、 乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (1R,2R,3S,10aS)-decahydropyrido[1,2-a]azepine-1,2,3-triyl triacetate
  参考文献：
  名称：

  A short and common stereoselective approach to 5/6, 6/6, 6/7 bicyclic aza sugars

  摘要：

  An efficient and highly stereoselective approach to bicyclic aza sugars is described using Grignard reaction on an N-benzyl imine derived from 3-O-benzyl-1,2-O-isopropylidine-alpha-D-xylo-pentodialdofuranose, ring closing metathesis, and reductive cyclization as key steps. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.038
• 作为产物：
  描述：

  在 palladium on activated charcoal 、 氢气 、 palladium(II) hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 (1R,2R,3S,10aS)-decahydropyrido[1,2-a]azepine-1,2,3-triol
  参考文献：
  名称：

  A short and common stereoselective approach to 5/6, 6/6, 6/7 bicyclic aza sugars

  摘要：

  An efficient and highly stereoselective approach to bicyclic aza sugars is described using Grignard reaction on an N-benzyl imine derived from 3-O-benzyl-1,2-O-isopropylidine-alpha-D-xylo-pentodialdofuranose, ring closing metathesis, and reductive cyclization as key steps. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.038

文献信息

• A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides
  作者：Ning Wang、Li-He Zhang、Xin-Shan Ye

  DOI：10.1039/b923180c

  日期：——

  A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted δ-lactams. The δ-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing

  一种简便，通用和立体选择性的双环多羟基化生物碱的合成方法 粟精胺描述了类似物。合成途径从甲基吡喃糖苷开始。关键步骤涉及从烯烃到高产率的快速一锅串联反应ñ取代的δ-内酰胺。δ-内酰胺经立体选择性乙烯基化得到二烯，然后进行闭环复分解反应生成环化产物。所得双环化合物的官能团转化以良好的产率提供了多种多羟基化生物碱。
• A short and common stereoselective approach to 5/6, 6/6, 6/7 bicyclic aza sugars
  作者：B. Chandrasekhar、B. Venkateswara Rao、K. Veera Mohana Rao、B. Jagadeesh

  DOI：10.1016/j.tetasy.2009.03.038

  日期：2009.6

  An efficient and highly stereoselective approach to bicyclic aza sugars is described using Grignard reaction on an N-benzyl imine derived from 3-O-benzyl-1,2-O-isopropylidine-alpha-D-xylo-pentodialdofuranose, ring closing metathesis, and reductive cyclization as key steps. (C) 2009 Elsevier Ltd. All rights reserved.