(3R,4S)-3,4-dibenzyloxy-5-(benzyloxymethyl)nona-1,8-dien-5-ol | 507238-29-1

• 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: (3R,4S)-3,4-dibenzyloxy-5-(benzyloxymethyl)nona-1,8-dien-5-ol
• 英文别名: (3R,4S)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)nona-1,8-dien-5-ol
• CAS: 507238-29-1
• 化学式: C₃₁H₃₆O₄
• 分子量: 472.624
• InChiKey: OCUAIWFYWPASJW-AWZUCMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3,4-dibenzyloxy-5-(benzyloxymethyl)nona-1,8-dien-5-ol 在 palladium on activated charcoal RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四氧化锇 、 氢气 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 、 叔丁醇 为溶剂， 反应 190.0h， 生成 (1S,2S,3R,4S,5S)-1-(hydroxymethyl)cyclohepta-1,2,3,4,5-pentol
  参考文献：
  名称：

  Synthesis of seven- and eight-membered carbasugar analogs via ring-closing metathesis and their inhibitory activities toward glycosidases

  摘要：

  An expeditious and efficient synthesis of new enantiopure polyhydroxylated seven- and eight-membered carbocycles is described starting from 2,3.5-tri-O-benzyl-D-arabinose. The key cyclization step involves ring closing metathesis of 1,8- and 1,9-dienes using Grubbs' catalyst. All of the new carbasugar analogs synthesized were evaluated as glycosidase inhibitors. Contrary to Our expectations, (1 S,2S,3R,4R,5R)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol which has the beta-D-mannopyranose configuration for C(1)-C(5) inhibits alpha- and beta-glucosidases, whereas its diepimer (1S,2S,3R,4S,5S)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol, which has the alpha-D-glucopyranose configuration, is not recognised by these enzymes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00654-7
• 作为产物：
  描述：

  (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3R,4S)-3,4-dibenzyloxy-5-(benzyloxymethyl)nona-1,8-dien-5-ol
  参考文献：
  名称：

  从d-阿拉伯糖高效合成8-氧杂双环[3.2.1]辛烷衍生物

  摘要：

  我们对TIBAL促进的Claisen重排反应和闭环复分解（RCM）的研究导致了从d-阿拉伯糖合成多官能七元羧化糖合成子的有效合成途径的发展。而且，通过BCl 3或碘化物促进的分子内亲电加成反应实现了8-氧杂双环[3.2.1]辛烷衍生物10和13的构建，所述区域选择性和立体选择性。

  DOI：

  10.1016/j.tetasy.2007.08.033

文献信息

• Synthesis of seven- and eight-membered carbasugar analogs via ring-closing metathesis and their inhibitory activities toward glycosidases
  作者：Yves Blériot、André Giroult、Jean-Maurice Mallet、Eliazar Rodriguez、Pierre Vogel、Pierre Sinaÿ

  DOI：10.1016/s0957-4166(02)00654-7

  日期：2002.11

  An expeditious and efficient synthesis of new enantiopure polyhydroxylated seven- and eight-membered carbocycles is described starting from 2,3.5-tri-O-benzyl-D-arabinose. The key cyclization step involves ring closing metathesis of 1,8- and 1,9-dienes using Grubbs' catalyst. All of the new carbasugar analogs synthesized were evaluated as glycosidase inhibitors. Contrary to Our expectations, (1 S,2S,3R,4R,5R)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol which has the beta-D-mannopyranose configuration for C(1)-C(5) inhibits alpha- and beta-glucosidases, whereas its diepimer (1S,2S,3R,4S,5S)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol, which has the alpha-D-glucopyranose configuration, is not recognised by these enzymes. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Efficient synthesis of 8-oxa-bicyclo[3.2.1]octane derivatives from d-arabinose
  作者：Yi Liu、Tian-Xiang Han、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.tetasy.2007.08.033

  日期：2007.9

  Our studies of the TIBAL-promoted Claisen rearrangement reaction and ring-closing metathesis (RCM) resulted in the development of an efficient synthetic route to polyfunctional seven-membered carbasugar synthons from d-arabinose. Moreover, the construction of 8-oxa-bicyclo[3.2.1]octane derivatives 10 and 13 was achieved by BCl3 or iodide-promoted intramolecular electrophilic addition reactions, which

  我们对TIBAL促进的Claisen重排反应和闭环复分解（RCM）的研究导致了从d-阿拉伯糖合成多官能七元羧化糖合成子的有效合成途径的发展。而且，通过BCl 3或碘化物促进的分子内亲电加成反应实现了8-氧杂双环[3.2.1]辛烷衍生物10和13的构建，所述区域选择性和立体选择性。