5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine | 162992-53-2

• 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: 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine
• 英文别名: (2S,3R,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-2-(hydroxymethyl)pyrrolidine；[(2S,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidin-2-yl]methanol
• CAS: 162992-53-2
• 化学式: C₂₇H₃₁NO₄
• 分子量: 433.547
• InChiKey: MPFNEVRQSMZOOM-FICKONGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以100%的产率得到2,5-二(羟基甲基)-3,4-吡咯烷二醇
  参考文献：
  名称：

  有效和立体发散地合成聚羟基吡咯烷酮的糖基方法

  摘要：

  据报道，由3,4,6-三-O-苄基-d-葡糖醛4立体合成了两个多羟基吡咯烷的非对映异构体，涉及裂解-再循环策略。半缩醛7从己烯糖得到4上LiAlH，在还原4，得到二醇8。选择性乙酰化8至11，然后Mitsunobu环化产生了多种保护的聚羟基吡咯烷12。氧化11和随后的立体选择性还原导致20中，C-5差向异构体的11，其在光延环化，得到polyhydroxypyrrolidine21。使用在MeOH中的Na 2 CO 3对12和21的乙酰基进行选择性脱保护。与过量的Mg的MeOH一起加热时，聚羟基吡咯烷12和21同时进行N-脱甲苯基化和脱乙酰化，以定量收率分别得到氨基醇15和24。15和24的催化氢化分别定量地提供了多羟基吡咯烷2和3。

  DOI：

  10.1016/j.tet.2005.11.037
• 作为产物：
  描述：

  2,5-二(羟基甲基)-3,4-吡咯烷二醇 在 氢氧化钾 、 sodium hydride 、 碳酸氢钠 、 potassium iodide 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 37.0h， 生成 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors

  摘要：

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.

  DOI：

  10.1021/jo00111a007

文献信息

• Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors
  作者：Chi-Huey Wong、Louis Provencher、John A. Porco、Sang-Hun Jung、Yi-Fong Wang、Lihren Chen、Ruo Wang、Darryl H. Steensma

  DOI：10.1021/jo00111a007

  日期：1995.3

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.
• A glycal approach towards an efficient and stereodivergent synthesis of polyhydroxypyrrolidines
  作者：Vipin Kumar、Namakkal G. Ramesh

  DOI：10.1016/j.tet.2005.11.037

  日期：2006.2

  A stereo-defined synthesis of two diastereomers of polyhydroxypyrrolidines from 3,4,6-tri-O-benzyl-d-glucal 4 involving a cleavage–recyclization strategy is reported. Hemiacetal 7 obtained from glucal 4, upon reduction with LiAlH4 afforded diol 8. Selective acetylation of 8 to 11, followed by Mitsunobu cyclization yielded the diversely protected polyhydroxypyrrolidine 12. Oxidation of 11 and subsequent

  据报道，由3,4,6-三-O-苄基-d-葡糖醛4立体合成了两个多羟基吡咯烷的非对映异构体，涉及裂解-再循环策略。半缩醛7从己烯糖得到4上LiAlH，在还原4，得到二醇8。选择性乙酰化8至11，然后Mitsunobu环化产生了多种保护的聚羟基吡咯烷12。氧化11和随后的立体选择性还原导致20中，C-5差向异构体的11，其在光延环化，得到polyhydroxypyrrolidine21。使用在MeOH中的Na 2 CO 3对12和21的乙酰基进行选择性脱保护。与过量的Mg的MeOH一起加热时，聚羟基吡咯烷12和21同时进行N-脱甲苯基化和脱乙酰化，以定量收率分别得到氨基醇15和24。15和24的催化氢化分别定量地提供了多羟基吡咯烷2和3。