(3S,4R)-3-O-benzyl-4,5-di-O-tert-butyldimethylsilyl-3,4,5-trihydroxypentan-1-al | 1410003-28-9

• 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: (3S,4R)-3-O-benzyl-4,5-di-O-tert-butyldimethylsilyl-3,4,5-trihydroxypentan-1-al
• 英文别名: (3S,4R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-3-phenylmethoxypentanal
• CAS: 1410003-28-9
• 化学式: C₂₄H₄₄O₄Si₂
• 分子量: 452.782
• InChiKey: BXGNIPKNCKVRAO-FCHUYYIVSA-N

物化性质

• 沸点：
  458.4±45.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-O-benzyl-4,5-di-O-tert-butyldimethylsilyl-3,4,5-trihydroxypentan-1-al 在 盐酸 、 lithium aluminium tetrahydride 、 水 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、 氯化铵 、 戴斯-马丁氧化剂 、 臭氧 、 三乙胺 、 sodium bromide 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 46.25h， 生成 (1S,2R,3S,4R)-1-O-benzyl-4-hydroxymethyl-cyclopentane-1,2,3-triol
  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：

  (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

文献信息

• (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.