(4aS,5aR,9aS,9bS,9cS)-8,8-Dimethyl-4a,5a,6,9a,9b,9c-hexahydro-3H-4,5,7,9-tetraoxa-pentaleno[1,6-ab]naphthalen-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (4aS,5aR,9aS,9bS,9cS)-8,8-Dimethyl-4a,5a,6,9a,9b,9c-hexahydro-3H-4,5,7,9-tetraoxa-pentaleno[1,6-ab]naphthalen-1-one
• 英文别名: (1S,2S,7R,9S,15S)-4,4-dimethyl-3,5,8,10-tetraoxatetracyclo[7.5.1.02,7.012,15]pentadec-12-en-14-one
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: WUPQHBSFJREWCT-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4aS,5aR,9aS,9bS,9cS)-8,8-Dimethyl-4a,5a,6,9a,9b,9c-hexahydro-3H-4,5,7,9-tetraoxa-pentaleno[1,6-ab]naphthalen-1-one 在 吡啶 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 生成 (2aR,6aS,6bR,7S,9sS)-7-acetyloxy-5,5'-dimethyl-1,2a,3,5,6a,6b,7,9a-octahydro-4,6-dioxacyclohexa[e]cyclopenta[c]pyran-9-methanol acetate
  参考文献：
  名称：

  手性和高度官能化的环戊烷的合成

  摘要：

  双杂环吡喃吡喃糖苷3和9中糖苷基C1O-外切键处的缩醛部分的意外还原是合成手性和高度官能化的环戊烷的一种简单而新的方法。

  DOI：

  10.1016/s0040-4039(00)02320-0

文献信息

• DIBALH mediated reduction of the acetal moiety on perhydrofuro[2,3-b]pyran derivatives
  作者：José Marco-Contelles、Juliana Ruiz-Caro

  DOI：10.1016/s0008-6215(01)00200-2

  日期：2001.9

  The reaction of DIBALH with bis(heteroannulated)-pyranosides containing the perhydrofuro[2,3-b]pyran moiety is described. The hydride attack at the anomeric carbon (C-9a) resulted in the exclusive tetrahydrofuran ring opening. The selectivity of this reaction has been evaluated as other benzylidene acetals built on these substrates remain practically or partially unaltered in these conditions depending on the steric volume of the O-protecting group located at C-4 (TBDMS vs. Me). This protocol can be considered as a new entry for the synthesis of chiral and highly functionalized cyclopentanes. (C) 2001 Elsevier Science Ltd. All rights reserved.