tert-butyl N-[(2S,3S)-1-[(2S)-2-[[dimethoxy(oxido)phosphaniumyl]-hydroxymethyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamate | 603956-51-0

• 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: tert-butyl N-[(2S,3S)-1-[(2S)-2-[[dimethoxy(oxido)phosphaniumyl]-hydroxymethyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamate
• CAS: 603956-51-0
• 化学式: C₁₈H₃₅N₂O₇P
• 分子量: 422.459
• InChiKey: HYNSBQICIVDNRG-AHZXVHSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S,3S)-1-[(2S)-2-[[dimethoxy(oxido)phosphaniumyl]-hydroxymethyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamate 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以41%的产率得到tert-butyl N-[(2S,3S)-1-[(2S)-2-[[dimethoxy(oxido)phosphaniumyl]-fluoromethyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamate
  参考文献：
  名称：

  β-Fluorinated proline derivatives: potential transition state inhibitors for proline selective serine dipeptidases

  摘要：

  Three new types of beta-fluorinated proline derivatives were synthesized as potential transition state inhibitors for proline selective serine dipeptidases. The fluorophosponate derived from protected proline was tested as a Wadsworth-Horner-Emmons reagent for the synthesis of fluoro-olefin-containing pseudodipeptides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02764-8
• 作为产物：
  描述：

  (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.33h， 生成 tert-butyl N-[(2S,3S)-1-[(2S)-2-[[dimethoxy(oxido)phosphaniumyl]-hydroxymethyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamate
  参考文献：
  名称：

  β-Fluorinated proline derivatives: potential transition state inhibitors for proline selective serine dipeptidases

  摘要：

  Three new types of beta-fluorinated proline derivatives were synthesized as potential transition state inhibitors for proline selective serine dipeptidases. The fluorophosponate derived from protected proline was tested as a Wadsworth-Horner-Emmons reagent for the synthesis of fluoro-olefin-containing pseudodipeptides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02764-8

文献信息

• β-Fluorinated proline derivatives: potential transition state inhibitors for proline selective serine dipeptidases
  作者：Pieter Van der Veken、Kristel Senten、István Kertèsz、Achiel Haemers、Koen Augustyns

  DOI：10.1016/s0040-4039(02)02764-8

  日期：2003.1

  Three new types of beta-fluorinated proline derivatives were synthesized as potential transition state inhibitors for proline selective serine dipeptidases. The fluorophosponate derived from protected proline was tested as a Wadsworth-Horner-Emmons reagent for the synthesis of fluoro-olefin-containing pseudodipeptides. (C) 2003 Elsevier Science Ltd. All rights reserved.