tert-butyl N-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5R)-5-[(1S)-1-hydroxytetradec-2-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]carbamate | 182073-44-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5R)-5-[(1S)-1-hydroxytetradec-2-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]carbamate
• CAS: 182073-44-5
• 化学式: C₃₂H₆₁NO₆Si
• 分子量: 583.925
• InChiKey: NNWIPBYIRAVRPY-LAJGZZDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.71
• 重原子数：
  40
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5R)-5-[(1S)-1-hydroxytetradec-2-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]carbamate 在 Lindlar's catalyst 咪唑 、 喹啉 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 ((S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-{(4S,5S)-5-[(Z)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  An expeditious and practical synthetic process for phytosphingosine and tetrahydroxy-LCB from D-glutamic acid

  摘要：

  For the asymmetric synthesis of phytosphingosine and 2-amino-1,3,4,5-tetrahydroxyoctadecene, the long chain base (LCB) part of novel cerebrosides, a simple and short synthetic route is described featuring the elabortion of the functionalized homochiral lactam derived from D-glutamic acid as a common structural unit. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00254-6
• 作为产物：
  描述：

  tert-butyl (2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 在 sodium tetrahydroborate 、 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 异丙醇 、 丙酮 为溶剂， 生成 tert-butyl N-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5R)-5-[(1S)-1-hydroxytetradec-2-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]carbamate
  参考文献：
  名称：

  An expeditious and practical synthetic process for phytosphingosine and tetrahydroxy-LCB from D-glutamic acid

  摘要：

  For the asymmetric synthesis of phytosphingosine and 2-amino-1,3,4,5-tetrahydroxyoctadecene, the long chain base (LCB) part of novel cerebrosides, a simple and short synthetic route is described featuring the elabortion of the functionalized homochiral lactam derived from D-glutamic acid as a common structural unit. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00254-6

文献信息

• An expeditious and practical synthetic process for phytosphingosine and tetrahydroxy-LCB from D-glutamic acid
  作者：Hidemi Yoda、Tetsuhiro Oguchi、Kunihiko Takabe

  DOI：10.1016/0957-4166(96)00254-6

  日期：1996.7

  For the asymmetric synthesis of phytosphingosine and 2-amino-1,3,4,5-tetrahydroxyoctadecene, the long chain base (LCB) part of novel cerebrosides, a simple and short synthetic route is described featuring the elabortion of the functionalized homochiral lactam derived from D-glutamic acid as a common structural unit. Copyright (C) 1996 Published by Elsevier Science Ltd