3(R)-(tert-butyldimethylsilanyloxy)-3-[1-(1'(S)-α-methylbenzyl)-aziridin-2(R)-yl]-propionic acid tert-butyl ester | 312728-16-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3(R)-(tert-butyldimethylsilanyloxy)-3-[1-(1'(S)-α-methylbenzyl)-aziridin-2(R)-yl]-propionic acid tert-butyl ester
• 英文别名: tert-butyl (3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-[(2R)-1-[(1S)-1-phenylethyl]aziridin-2-yl]propanoate
• CAS: 312728-16-8
• 化学式: C₂₃H₃₉NO₃Si
• 分子量: 405.653
• InChiKey: GRPKNCPWXADSQK-LVXUHDSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  38.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3(R)-(tert-butyldimethylsilanyloxy)-3-[1-(1'(S)-α-methylbenzyl)-aziridin-2(R)-yl]-propionic acid tert-butyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 5-acetoxy-4(R)-tert-butoxycarbonylamino-3(R)-(tert-butyldimethylsilanyloxy)-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of protected threo-β-hydroxy-l-glutamic acid using a chiral aziridine

  摘要：

  Threo-beta-hydroxy-L-glutamic acid derivatives with different carboxylic acid protecting groups were stereoselectively prepared from a chiral aziridine-2-carboxylate using an aldol reaction, stereoselective ketone reduction, and aziridine ring transformation. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00311-6
• 作为产物：
  描述：

  ethyl 1-[(S)-1-phenylethyl]aziridine-(R)-carboxylate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 TEA 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 19.0h， 生成 3(R)-(tert-butyldimethylsilanyloxy)-3-[1-(1'(S)-α-methylbenzyl)-aziridin-2(R)-yl]-propionic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of protected threo-β-hydroxy-l-glutamic acid using a chiral aziridine

  摘要：

  Threo-beta-hydroxy-L-glutamic acid derivatives with different carboxylic acid protecting groups were stereoselectively prepared from a chiral aziridine-2-carboxylate using an aldol reaction, stereoselective ketone reduction, and aziridine ring transformation. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00311-6

文献信息

• Stereoselective synthesis of protected threo-β-hydroxy-l-glutamic acid using a chiral aziridine
  作者：Chan Sun Park、Hawn Geun Choi、Hyunjoo Lee、Won Koo Lee、Hyun-Joon Ha*

  DOI：10.1016/s0957-4166(00)00311-6

  日期：2000.8

  Threo-beta-hydroxy-L-glutamic acid derivatives with different carboxylic acid protecting groups were stereoselectively prepared from a chiral aziridine-2-carboxylate using an aldol reaction, stereoselective ketone reduction, and aziridine ring transformation. (C) 2000 Published by Elsevier Science Ltd.