(3aS,4S,6aS)-tert-butyl 4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate | 178456-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3aS,4S,6aS)-tert-butyl 4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• 英文别名: tert-butyl (3aS,6S,6aS)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 178456-74-1
• 化学式: C₁₉H₃₅NO₆Si
• 分子量: 401.576
• InChiKey: KADRSKVHGJRTKT-IHRRRGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6aS)-tert-butyl 4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 吡啶 、 2,6-二甲基吡啶 、 甲醇 、 三乙基硅烷 、 sodium periodate 、 草酰氯 、 三氟甲磺酸三甲基硅酯 、 dimethyl sulfide borane 、 三氟化硼乙醚 、 四丁基氟化铵 、 二异丁基氢化铝 、 三乙基硼氢化锂 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 87.75h， 生成 (1S,2R,8R,8aS)-octahydro-1,2,8-indolizidinetriol
  参考文献：
  名称：

  A facile synthesis of 1,4-dideoxy-1,4-imino-l-ribitol (LRB) and (−)-8a-epi-swainsonine from d-glutamic acid

  摘要：

  A facile synthesis of (-)-8a-epi-swainsonine 2 and 1,4-dideoxy-1,4-imino-L-ribitol (LRB) 4 has been achieved by using the versatile building block 3, which was available from cheap D-glutamic acid. The new forming stereogenic center in synthesis of 2 was constructed by highly selective reduction of the ketone 13 with Li(t-BuO)(3)AlH in THF (dr=95:5). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.075
• 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 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 丙酮 为溶剂， 生成 (3aS,4S,6aS)-tert-butyl 4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
  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

• Asymmetric synthesis of ceramide sphingolipid based on (2S,3S,4S)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine lactam
  作者：Wen-Feng Huang、Qian-Ru Li、Lu-Men Chao、Xin-Sheng Lei、Bang-Guo Wei

  DOI：10.1016/j.tetlet.2010.06.001

  日期：2010.8

  A facile approach to the versatile chiral building block 2 was developed based on glutamic acid, whereby a new method for asymmetric synthesis of sex pheromone 1 was explored from cheap glutamic acid.

  基于谷氨酸开发了一种通用的手性结构单元2的简便方法，从而从廉价的谷氨酸​​中探索了一种不对称合成性信息素1的新方法。
• Novel asymmetric synthesis of penaresidin B as a potent actomyosin ATPase activator
  作者：Hidemi Yoda、Tetsuhiro Oguchi、Kunihiko Takabe

  DOI：10.1016/s0040-4039(97)00603-5

  日期：1997.5

  An efficient and novel synthetic process is described for the preparation of an azetidine ring with the contiguous stereogenic centers and the total synthesis of penaresidin B by featuring the elaboration of the functionalized homochiral lactam derived from D-glutamic acid. (C) 1997 Elsevier Science Ltd.
• Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline
  作者：Franca Zanardi、Lucia Battistini、Marika Nespi、Gloria Rassu、Pietro Spanu、Mara Cornia、Giovanni Casiraghi

  DOI：10.1016/0957-4166(96)00123-1

  日期：1996.4

  Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon. Copyright (C) 1996 Elsevier Science Ltd
• 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
• A facile synthesis of 1,4-dideoxy-1,4-imino-l-ribitol (LRB) and (−)-8a-epi-swainsonine from d-glutamic acid
  作者：Xiao-Ling Wang、Wen-Feng Huang、Xin-Sheng Lei、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1016/j.tet.2011.04.075

  日期：2011.7

  A facile synthesis of (-)-8a-epi-swainsonine 2 and 1,4-dideoxy-1,4-imino-L-ribitol (LRB) 4 has been achieved by using the versatile building block 3, which was available from cheap D-glutamic acid. The new forming stereogenic center in synthesis of 2 was constructed by highly selective reduction of the ketone 13 with Li(t-BuO)(3)AlH in THF (dr=95:5). (C) 2011 Elsevier Ltd. All rights reserved.