[(1S,2R,3R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-hex-5-enyl]-carbamic acid benzyl ester | 269715-82-4

• 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: [(1S,2R,3R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-hex-5-enyl]-carbamic acid benzyl ester
• CAS: 269715-82-4
• 化学式: C₂₂H₃₇NO₄Si
• 分子量: 407.626
• InChiKey: CZGMVFWDKRZCSX-MISYRCLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 [(1S,2R,3R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-hex-5-enyl]-carbamic acid benzyl ester 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以27%的产率得到(4S,5R,6R)-6-Allyl-3-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-[1,3]oxazinan-2-one
  参考文献：
  名称：

  Stereoselective synthesis of a tricyclic guanidinium model of cylindrospermopsin

  摘要：

  An 11-step enantioselective synthesis of the A-ring of cylindrospermopsin is described using an intramolecular conjugate addition as the key step to forming the piperidine ring. Further elaboration generates a tricyclic guanidine via a sequential double displacement strategy as a model for the cylindrospermopsin guanidinium core. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02348-5
• 作为产物：
  描述：

  [(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-propyl]-carbamic acid benzyl ester 在 三氟化硼乙醚 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 [(1S,2R,3R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2-methyl-hex-5-enyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Stereoselective synthesis of a tricyclic guanidinium model of cylindrospermopsin

  摘要：

  An 11-step enantioselective synthesis of the A-ring of cylindrospermopsin is described using an intramolecular conjugate addition as the key step to forming the piperidine ring. Further elaboration generates a tricyclic guanidine via a sequential double displacement strategy as a model for the cylindrospermopsin guanidinium core. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02348-5