(4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene | 1239889-27-0

• 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: (4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene
• 英文别名: tert-butyl-[(2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylmethoxyhex-5-enoxy]-dimethylsilane
• CAS: 1239889-27-0
• 化学式: C₂₅H₄₆O₃Si₂
• 分子量: 450.809
• InChiKey: ZNNKTUJBWYJYOI-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以85.9%的产率得到(3S,4R)-3-O-benzyl-4,5-di-O-tert-butyldimethylsilyl-3,4,5-trihydroxypentan-1-al
  参考文献：
  名称：

  (R)-2,3-O-Cyclohexylideneglyceraldehyde: a useful template for a simple entry into carbafuranose stereoisomers

  摘要：

  (R)-2,3-O-Cyclohexylideneglyceraldehyde 1 provides a simple route for the preparation of carbafuranoses. This has been exemplified by the preparation of 10c and 10d, the derivatives of carba D-xylofuranose and carba-L-arabinofuranose respectively, starting from homoallylic alcohol 2a derived from 1. The key step in this protocol was the intramolecular allylation of 9 promoted by several metals under wet conditions that resulted in the construction of the carbafuranose skeleton of 10. The potential of several metals regarding the efficacy and stereoselectivity of this crucial intramolecular allylation reaction has been studied. The moderate stereoselectivity in all of the successful intramolecular allylations of 9 yielding both D-10c and L-10d as the major products contributed significantly in attaining stereo-divergence in this route. The utility of this route was due to the easy availability of 1, and the operational simplicity as well as scalability of all of the reactions involved. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.007
• 作为产物：
  描述：

  (2R,3S)-3-(benzyloxy)hex-5-ene-1,2-diol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以85%的产率得到(4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene
  参考文献：
  名称：

  基于关键闭环易位的五元环碳节糖的简明合成

  摘要：

  从容易获得的（R）-2,3- O-异亚丙基甘油醛（2）到关键的闭环复分解（RCM），以高的总收率实现了一种简单而有效的合成五元环碳节糖的方法。我们还通过准备在有效的抗病毒核苷N-MCT 1中提供的核心双环[3.1.0]己烷骨架来证实其可行性。

  DOI：

  10.1016/j.tetlet.2010.05.069

文献信息

• Concise synthesis of five-membered ring carbasugars based on key ring-closing metathesis
  作者：Ya-Xi Yang、Zheng Li、Hui-Jin Feng、Guo-Rong Chen、Yuan-Chao Li

  DOI：10.1016/j.tetlet.2010.05.069

  日期：2010.7

  A simple and efficient approach to the synthesis of five-membered ring carbasugars is achieved starting from readily available (R)-2,3-O-isopropylideneglyceraldehyde (2) through key ring-closing metathesis (RCM) in high overall yield. We have also confirmed its viability by preparing the core bicyclo [3.1.0] hexane framework presented in the potent antiviral nucleoside N-MCT 1.

  从容易获得的（R）-2,3- O-异亚丙基甘油醛（2）到关键的闭环复分解（RCM），以高的总收率实现了一种简单而有效的合成五元环碳节糖的方法。我们还通过准备在有效的抗病毒核苷N-MCT 1中提供的核心双环[3.1.0]己烷骨架来证实其可行性。
• (R)-2,3-O-Cyclohexylideneglyceraldehyde: a useful template for a simple entry into carbafuranose stereoisomers
  作者：Sibanarayan Tripathy、Angshuman Chattopadhyay

  DOI：10.1016/j.tetasy.2012.09.007

  日期：2012.10

  (R)-2,3-O-Cyclohexylideneglyceraldehyde 1 provides a simple route for the preparation of carbafuranoses. This has been exemplified by the preparation of 10c and 10d, the derivatives of carba D-xylofuranose and carba-L-arabinofuranose respectively, starting from homoallylic alcohol 2a derived from 1. The key step in this protocol was the intramolecular allylation of 9 promoted by several metals under wet conditions that resulted in the construction of the carbafuranose skeleton of 10. The potential of several metals regarding the efficacy and stereoselectivity of this crucial intramolecular allylation reaction has been studied. The moderate stereoselectivity in all of the successful intramolecular allylations of 9 yielding both D-10c and L-10d as the major products contributed significantly in attaining stereo-divergence in this route. The utility of this route was due to the easy availability of 1, and the operational simplicity as well as scalability of all of the reactions involved. (C) 2012 Elsevier Ltd. All rights reserved.