(+)-1,1'-methylenedi[(1S,1'S,3S,3'S,5S,5'S)-8-oxabicyclo[3.2.1]oct-6-en-3-yl] diacetate | 339266-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (+)-1,1'-methylenedi[(1S,1'S,3S,3'S,5S,5'S)-8-oxabicyclo[3.2.1]oct-6-en-3-yl] diacetate
• 英文别名: [(1S,3S,5S)-1-[[(1S,3S,5S)-3-acetyloxy-8-oxabicyclo[3.2.1]oct-6-en-1-yl]methyl]-8-oxabicyclo[3.2.1]oct-6-en-3-yl] acetate
• CAS: 339266-73-8
• 化学式: C₁₉H₂₄O₆
• 分子量: 348.396
• InChiKey: ZIXDAZOHQCGCKB-SVMUCYCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-1,1'-methylenedi[(1S,1'S,3S,3'S,5S,5'S)-8-oxabicyclo[3.2.1]oct-6-en-3-yl] diacetate 在 吡啶 、 4-二甲氨基吡啶 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 1,1'-methylenedi[(3S,3'S,4S,4'S,6S,6'S)-6-acetoxy-6-chlorocyclohept-1-en-4-yl] bis(p-methoxybenzoate)
  参考文献：
  名称：

  Synthesis of 1,1′-methylenedi[(1 R ,1′ R ,3 R ,3′ R ,5 R ,5′ R )-8-oxabicyclo[3.2.1]oct-6-en-3-ol] and derivatives: precursors of long-chain polyketides

  摘要：

  Racemic 1,1'-methylene[(1RS, 1'RS, 3RS, 3'RS, 5RS, 5'RS)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] ((+/-)-6) derived from 2,2'-methylenedifuran has been resolved kinetically with Candida cylindracea lipase-catalysed transesterification giving 1,1'-methylenedi[(1R, 1'R, 3R, 3'R, 5R, 5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] (-)-6 (30% yield, 98% ee) and 1,1'-methylenedi[(1S, 1'S, 3S, 3'S, 5S, 5'S)-8-oxabicyclo[3.2.1]oct-6-en-3-yl] diacetate (+)-8, (40% yield, 98% ee). These compounds have been converted into 1,1'-methylenedi[(4S, 4'S, 6S, 6'S)- and (4R, 4'R, 6R, 6'R)-cyclohept-1-en-4,6-diyl] derivatives. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00475-4

文献信息

• An Expeditious, Non-Iterative, and Asymmetric Synthesis of 3,5,7,9,11,13,15-Heptahydroxypentadecanals
  作者：Sandrine Gerber-Lemaire、Pierre Vogel

  DOI：10.1002/ejoc.200300224

  日期：2003.8

  6'R)-3,3'-methylenebis6-[(benzyloxy)methoxy]cyclohept-3-en-1 -ol} followed by the diastereo-selective reduction of the resulting beta-hydroxy ketone intermediates gives a rapid route to long-chain polyketides bearing unsymmetrical functions at their terminal positions. These can easily be converted into enantiomerically pure long-chain 1,3-polyol fragments. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  (1R,1'R,6R,6'R)-3,3'-亚甲基双6-[(苄氧基)甲氧基]环庚-3-en-1-ol}的臭氧分解，然后非对映选择性还原由此产生的 β-羟基酮中间体为在其末端位置具有不对称功能的长链聚酮化合物提供了一条快速途径。这些可以很容易地转化为对映异构纯的长链 1,3-多元醇片段。((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)。