[(S)-1-((1S,2S)-1-Benzyl-2-hydroxy-4-trimethylsilanylmethyl-pent-4-enylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester | 178427-87-7

• 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: [(S)-1-((1S,2S)-1-Benzyl-2-hydroxy-4-trimethylsilanylmethyl-pent-4-enylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester
• CAS: 178427-87-7
• 化学式: C₂₆H₄₄N₂O₄Si
• 分子量: 476.732
• InChiKey: VRVWHUUJYWOEPB-VABKMULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  87.66
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(S)-1-((1S,2S)-1-Benzyl-2-hydroxy-4-trimethylsilanylmethyl-pent-4-enylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 在 chromium dichloride 、 溴 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 54.0h， 生成 [(S)-1-((4S,5S)-4-Benzyl-5-{2-[(4S,5S)-4-benzyl-3-((S)-2-tert-butoxycarbonylamino-3-methyl-butyryl)-2,2-dimethyl-oxazolidin-5-ylmethyl]-allyl}-2,2-dimethyl-oxazolidine-3-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  CrCl2 Mediated addition of allylic halides or phosphates to N-protected α-amino aldehydes. Stereocontrolled synthesis of a new core for C2 symmetric HIV-protease inhibitors

  摘要：

  The addition of gamma-monosubstituted allylchromium(lll) reagents to N-protected alpha-amino aldehydes proceeds in a stereoconvergent manner in contrast with the case of the unsubstituted reagents, where the stereoselectivity depends on the nature of the group bonded to the nitrogen. The chromium(III) reagent derived from 3-chloromethyl-2-trimethylsilyl-1-propene was used to prepare a C-2 symmetric HIV-protease inhibitor. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00258-x
• 作为产物：
  描述：

  2-(氯甲基)烯丙基-三甲基硅烷 、 Boc-Val-Phe-CHO 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [(S)-1-((1S,2S)-1-Benzyl-2-hydroxy-4-trimethylsilanylmethyl-pent-4-enylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  CrCl2 Mediated addition of allylic halides or phosphates to N-protected α-amino aldehydes. Stereocontrolled synthesis of a new core for C2 symmetric HIV-protease inhibitors

  摘要：

  The addition of gamma-monosubstituted allylchromium(lll) reagents to N-protected alpha-amino aldehydes proceeds in a stereoconvergent manner in contrast with the case of the unsubstituted reagents, where the stereoselectivity depends on the nature of the group bonded to the nitrogen. The chromium(III) reagent derived from 3-chloromethyl-2-trimethylsilyl-1-propene was used to prepare a C-2 symmetric HIV-protease inhibitor. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00258-x

文献信息

• CrCl2 Mediated addition of allylic halides or phosphates to N-protected α-amino aldehydes. Stereocontrolled synthesis of a new core for C2 symmetric HIV-protease inhibitors
  作者：Paola Ciapetti、Massimo Falorni、Maurizio Taddei

  DOI：10.1016/0040-4020(96)00258-x

  日期：1996.5

  The addition of gamma-monosubstituted allylchromium(lll) reagents to N-protected alpha-amino aldehydes proceeds in a stereoconvergent manner in contrast with the case of the unsubstituted reagents, where the stereoselectivity depends on the nature of the group bonded to the nitrogen. The chromium(III) reagent derived from 3-chloromethyl-2-trimethylsilyl-1-propene was used to prepare a C-2 symmetric HIV-protease inhibitor. Copyright (C) 1996 Elsevier Science Ltd