(3S,4R,5S)-5-(benzyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)hex-1-en-3-yl diisopropylcarbamate | 762261-99-4

• 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,5S)-5-(benzyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)hex-1-en-3-yl diisopropylcarbamate
• 英文别名: [(3S,4R,5S)-4-hydroxy-5-phenylmethoxy-2-(trimethylsilylmethyl)hex-1-en-3-yl] N,N-di(propan-2-yl)carbamate
• CAS: 762261-99-4
• 化学式: C₂₄H₄₁NO₄Si
• 分子量: 435.679
• InChiKey: UYMMRDKGVDQIFV-WWNPGLIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-5-(benzyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)hex-1-en-3-yl diisopropylcarbamate 在 吡啶 、 4-二甲氨基吡啶 、 二甲基硫 、 臭氧 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-3-diisopropylcarbamoyloxy-6-methoxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of highly substituted 2,6-anti-configured tetrahydropyrans. First steps towards an efficient access to amphidinol 3 ring system

  摘要：

  Highly functionalised and polysubstituted tetrahydropyrans, akin to the middle core of the amphidinols, can be efficiently synthesised, with full stereocontrol and in good yields, using as key steps an anti-allylation reaction coupled with an intramolecular Sakurai cyclisation. Three approaches were devised in order to reach a broad range of substitution patterns. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.041
• 作为产物：
  描述：

  methyl (S)-2-(benzyloxy)propanoate 在 四氯化锡 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (3S,4R,5S)-5-(benzyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)hex-1-en-3-yl diisopropylcarbamate
  参考文献：
  名称：

  Stereoselective synthesis of functionalised triol units by SnCl4 promoted allylation of α-benzyloxyaldehydes: crucial role of the stoichiometry of the Lewis acid

  摘要：

  Enantiomerically pure syn-anti and syn-syn configured triol units are efficiently synthesized by the SnCl4 mediated allylation of chiral alpha-benzyloxyaldehydes with the uniquely functionalised allylstannane 9. Remarkably, the stereochemistry of the adducts is solely governed by the amount of Lewis acid employed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.084

文献信息

• Rapid and Versatile Synthesis of Functionalized Polyhydroxylated Fragments
  作者：Bernard Leroy、István E. Markó

  DOI：10.1021/ol016863u

  日期：2002.1.1

  [GRAPHICS]The condensation between a functionalized allylstannane and alpha-alkoxyaldehydes allows rapid access to complex and selectively protected trihydroxylated synthons. The stereocontrol of this process is strongly dependent upon the nature and the amount of the Lewis acid employed.
• Stereoselective synthesis of functionalised triol units by SnCl4 promoted allylation of α-benzyloxyaldehydes: crucial role of the stoichiometry of the Lewis acid
  作者：Christophe Dubost、Bernard Leroy、Istvan E. Markó、Bernard Tinant、Jean-Paul Declercq、Justin Bryans

  DOI：10.1016/j.tet.2004.06.084

  日期：2004.8

  Enantiomerically pure syn-anti and syn-syn configured triol units are efficiently synthesized by the SnCl4 mediated allylation of chiral alpha-benzyloxyaldehydes with the uniquely functionalised allylstannane 9. Remarkably, the stereochemistry of the adducts is solely governed by the amount of Lewis acid employed. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of highly substituted 2,6-anti-configured tetrahydropyrans. First steps towards an efficient access to amphidinol 3 ring system
  作者：Christophe Dubost、Istvan E. Markó、Justin Bryans

  DOI：10.1016/j.tetlet.2005.04.041

  日期：2005.6

  Highly functionalised and polysubstituted tetrahydropyrans, akin to the middle core of the amphidinols, can be efficiently synthesised, with full stereocontrol and in good yields, using as key steps an anti-allylation reaction coupled with an intramolecular Sakurai cyclisation. Three approaches were devised in order to reach a broad range of substitution patterns. (c) 2005 Elsevier Ltd. All rights reserved.