((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester | 269715-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: ((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester
• 英文别名: benzyl N-[(3R,4aS,6S,7R,8S)-6-hydroxy-8-(hydroxymethyl)-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl]carbamate
• CAS: 269715-94-8
• 化学式: C₁₉H₂₇N₃O₄
• 分子量: 361.441
• InChiKey: YCCBHKOKWMJXOS-GJVDQKBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  94.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以27%的产率得到(2aS,3R,4S,5aS,7R)-4-Hydroxy-3,7-dimethyl-2,2a,3,4,5,5a,6,7-octahydro-1,8,8b-triaza-acenaphthylene-1-carboxylic 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
• 作为产物：
  描述：

  1-[(2R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methylpiperidin-2-yl]propan-2-one 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 、 三苯基膦 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 ((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-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

文献信息

• Stereoselective synthesis of a tricyclic guanidinium model of cylindrospermopsin
  作者：Indrawan J. McAlpine、Robert W. Armstrong

  DOI：10.1016/s0040-4039(99)02348-5

  日期：2000.3

  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.