benzyl N-[[(2S,3R,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyl-6-(2-oxopropyl)piperidin-1-yl]-(phenylmethoxycarbonylamino)methylidene]carbamate | 269715-89-1

• 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: benzyl N-[[(2S,3R,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyl-6-(2-oxopropyl)piperidin-1-yl]-(phenylmethoxycarbonylamino)methylidene]carbamate
• CAS: 269715-89-1
• 化学式: C₃₉H₆₁N₃O₇Si₂
• 分子量: 740.1
• InChiKey: UTVQHUDHBJPFBQ-KOTXVPMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.08
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl N-[[(2S,3R,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyl-6-(2-oxopropyl)piperidin-1-yl]-(phenylmethoxycarbonylamino)methylidene]carbamate 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 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
• 作为产物：
  描述：

  [(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-hex-5-enyl]-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 、 臭氧 、 三乙胺 、 三苯基膦 、 mercury dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 benzyl N-[[(2S,3R,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyl-6-(2-oxopropyl)piperidin-1-yl]-(phenylmethoxycarbonylamino)methylidene]carbamate
  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.