3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)-1-hydroxy-pyrrolidin-2-yl)propionic acid ethyl ester | 948897-76-5

• 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: 3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)-1-hydroxy-pyrrolidin-2-yl)propionic acid ethyl ester
• 英文别名: ethyl 3-[(2S,3S,4S,5S)-5-[(1S)-1,2-bis(phenylmethoxy)ethyl]-1-hydroxy-3,4-bis(phenylmethoxy)pyrrolidin-2-yl]propanoate
• CAS: 948897-76-5
• 化学式: C₃₉H₄₅NO₇
• 分子量: 639.789
• InChiKey: YNCRPDZHNLFGPC-XNVAUQMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)-1-hydroxy-pyrrolidin-2-yl)propionic acid ethyl ester 在 samarium diiodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以68%的产率得到3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)pyrrolidin-2-yl)propionic acid ethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of β-1-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols and evaluation as UDP-galactopyranose mutase inhibitors

  摘要：

  The synthesis of 1-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols involving nitrone umpolung is described. The SmI2-induced key coupling proved highly stereoselective in favor of the beta-C-substituted products bearing a three-carbon chain at the pseudoanomeric position. Pyrrolidines 9 and 10, as well as the bicyclic compounds 8 and 11, exhibit weak inhibition of the activity of the UDP-galactopyranose mutase from Escherichia coli. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.059
• 作为产物：
  描述：

  (2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide 、 丙烯酸乙酯 在 samarium diiodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以68%的产率得到3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)-1-hydroxy-pyrrolidin-2-yl)propionic acid ethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of β-1-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols and evaluation as UDP-galactopyranose mutase inhibitors

  摘要：

  The synthesis of 1-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols involving nitrone umpolung is described. The SmI2-induced key coupling proved highly stereoselective in favor of the beta-C-substituted products bearing a three-carbon chain at the pseudoanomeric position. Pyrrolidines 9 and 10, as well as the bicyclic compounds 8 and 11, exhibit weak inhibition of the activity of the UDP-galactopyranose mutase from Escherichia coli. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.059

文献信息

• Novel Polyhydroxylated Cyclic Nitrones and <i>N</i>-Hydroxypyrrolidines through BCl₃-Mediated Deprotection
  作者：Stéphanie Desvergnes、Yannick Vallée、Sandrine Py

  DOI：10.1021/ol8007759

  日期：2008.7.17

  method to prepare a new class of carbohydrate-derived, enantiomerically pure polyhydroxypyrroline N-oxides from their alkoxy (protected) derivatives is presented. Boron trichloride is shown to cleave efficiently benzyl ethers and ketals without affecting the imine N-oxide functionality of nitrones. The same reagent (BCl3) also allowed the efficient synthesis of a polyhydroxylated N-hydroxypyrrolidine

  提出了一种从其烷氧基（被保护的）衍生物制备新型碳水化合物衍生的对映体纯的多羟基吡咯啉N-氧化物的通用方法。已显示三氯化硼可有效裂解苄基醚和缩酮，而不会影响硝酮的亚胺N-氧化物官能度。相同的试剂（BCl3）还允许有效地合成多羟基化的N-羟基吡咯烷，从而获得了一类新型的N-羟基亚氨基糖。
• Stereoselective synthesis of β-1-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols and evaluation as UDP-galactopyranose mutase inhibitors
  作者：Stéphanie Desvergnes、Valérie Desvergnes、Olivier R. Martin、Kenji Itoh、Hung-wen Liu、Sandrine Py

  DOI：10.1016/j.bmc.2007.06.059

  日期：2007.10

  The synthesis of 1-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols involving nitrone umpolung is described. The SmI2-induced key coupling proved highly stereoselective in favor of the beta-C-substituted products bearing a three-carbon chain at the pseudoanomeric position. Pyrrolidines 9 and 10, as well as the bicyclic compounds 8 and 11, exhibit weak inhibition of the activity of the UDP-galactopyranose mutase from Escherichia coli. (C) 2007 Elsevier Ltd. All rights reserved.