(2S,7S)-5-(1,3-dioxolane)-2,8-bis[N-benzyloxycarbonylamino]nonane-1,9-dioic acid dimethyl ester | 346441-81-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,7S)-5-(1,3-dioxolane)-2,8-bis[N-benzyloxycarbonylamino]nonane-1,9-dioic acid dimethyl ester
• 英文别名: methyl (2S)-4-[2-[(3S)-4-methoxy-4-oxo-3-(phenylmethoxycarbonylamino)butyl]-1,3-dioxolan-2-yl]-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 346441-81-4
• 化学式: C₂₉H₃₆N₂O₁₀
• 分子量: 572.612
• InChiKey: KSQLJYHGWCPWOB-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,7S)-5-(1,3-dioxolane)-2,8-bis[N-benzyloxycarbonylamino]nonane-1,9-dioic acid dimethyl ester 在 palladium on activated charcoal 氢气 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 盐酸 、 甲醇 为溶剂， -50.0~-20.0 ℃ 、482.63 kPa 条件下， 反应 33.0h， 生成 (3S,6R,9S) methyl 2-oxo-3-[N-(t-butoxycarbonyl)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylate
  参考文献：
  名称：

  An efficient approach to asymmetric synthesis of dipeptide β-turn mimetics: indolizidinone amino acids

  摘要：

  Azabicyclo[X.Y.0] alkane amino acids are rigid dipeptide P-turn mimetics with great potential applications for drug discovery. The lack of efficient methods to synthesize these compounds is a major bottleneck in this field. Herein we report an efficient approach to the enantiopure synthesis of (3S,6S,9S) and (3R,6R,9R) methyl 2-oxo-3-[N-(Boc/Cbz)amino]-1-azabicyclo[4,3,0]nonane-9-carboxylates 1. In this approach, the key intermediates 5a and 5b with different stereochemical configurations were efficiently constructed from the same precursor in high stereoselectivity via asymmetric hydrogenations using (S,S) or (R,R) Et-DUPHOS, Rh(I)-based catalysts. The process, starting from inexpensive diethyl 1,3-acetonedicarboxylate 2, can allow for the practical synthesis of this class of compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00409-9
• 作为产物：
  描述：

  1,3-丙酮二羧酸二乙酯 在 Rh(I)(COD)(S,S) Et-DUPHOS 三氟化硼乙醚 、 氢气 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 苯 为溶剂， -78.0~20.0 ℃ 、482.63 kPa 条件下， 反应 53.17h， 生成 (2S,7S)-5-(1,3-dioxolane)-2,8-bis[N-benzyloxycarbonylamino]nonane-1,9-dioic acid dimethyl ester
  参考文献：
  名称：

  An efficient approach to asymmetric synthesis of dipeptide β-turn mimetics: indolizidinone amino acids

  摘要：

  Azabicyclo[X.Y.0] alkane amino acids are rigid dipeptide P-turn mimetics with great potential applications for drug discovery. The lack of efficient methods to synthesize these compounds is a major bottleneck in this field. Herein we report an efficient approach to the enantiopure synthesis of (3S,6S,9S) and (3R,6R,9R) methyl 2-oxo-3-[N-(Boc/Cbz)amino]-1-azabicyclo[4,3,0]nonane-9-carboxylates 1. In this approach, the key intermediates 5a and 5b with different stereochemical configurations were efficiently constructed from the same precursor in high stereoselectivity via asymmetric hydrogenations using (S,S) or (R,R) Et-DUPHOS, Rh(I)-based catalysts. The process, starting from inexpensive diethyl 1,3-acetonedicarboxylate 2, can allow for the practical synthesis of this class of compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00409-9

文献信息

• An efficient approach to asymmetric synthesis of dipeptide β-turn mimetics: indolizidinone amino acids
  作者：Wei Wang、Chiyi Xiong、Victor J Hruby

  DOI：10.1016/s0040-4039(01)00409-9

  日期：2001.4

  Azabicyclo[X.Y.0] alkane amino acids are rigid dipeptide P-turn mimetics with great potential applications for drug discovery. The lack of efficient methods to synthesize these compounds is a major bottleneck in this field. Herein we report an efficient approach to the enantiopure synthesis of (3S,6S,9S) and (3R,6R,9R) methyl 2-oxo-3-[N-(Boc/Cbz)amino]-1-azabicyclo[4,3,0]nonane-9-carboxylates 1. In this approach, the key intermediates 5a and 5b with different stereochemical configurations were efficiently constructed from the same precursor in high stereoselectivity via asymmetric hydrogenations using (S,S) or (R,R) Et-DUPHOS, Rh(I)-based catalysts. The process, starting from inexpensive diethyl 1,3-acetonedicarboxylate 2, can allow for the practical synthesis of this class of compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.