(2R,3R,4R,5S)-5-benzyloxymethyl-3,4-dibenzyloxy-5-methylpyrrolidine | 944544-03-0

• 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: (2R,3R,4R,5S)-5-benzyloxymethyl-3,4-dibenzyloxy-5-methylpyrrolidine
• 英文别名: (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine；(2S,3R,4R,5R)-2-methyl-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidine
• CAS: 944544-03-0
• 化学式: C₂₇H₃₁NO₃
• 分子量: 417.548
• InChiKey: WDNUJFWYZYJLGM-IZIBRLFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-5-benzyloxymethyl-3,4-dibenzyloxy-5-methylpyrrolidine 、 溴甲苯 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以75%的产率得到(2R,3R,4R,5S)-1-benzyl-2-benzyloxymethyl-3,4-dibenzyloxy-5-methylpyrrolidine
  参考文献：
  名称：

  A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide

  摘要：

  A highly diastereoselective synthesis of enantio-enriched all trans-3,4-dibenzyloxyl-5-benzyloxymethyl-2-pyrrolidinone 13a was developed based on SmI2-mediated benzyloxymethylation of O,O'-dibenzyltartarimide. The versatility of 13a and its antipode as the key building blocks for the asymmetric synthesis of pyrrolidine azasugars and homoazasugars has been demonstrated by elaborating them into naturally occurring DAB 1 (1), LAB 1 (2), N-hydroxyethyl-DAB 1 (4), 6-deoxy-DMDP 7, and 5-epi-radicamine B 36 as well as the reductive ring-opening product 35. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.02.087
• 作为产物：
  描述：

  L-O,O-dibenzyltartaric acid 在 三乙基硅烷 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 三氟化硼乙醚 、 magnesium 、 三乙胺 、 乙酰氯 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 33.5h， 生成 (2R,3R,4R,5S)-5-benzyloxymethyl-3,4-dibenzyloxy-5-methylpyrrolidine
  参考文献：
  名称：

  A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide

  摘要：

  A highly diastereoselective synthesis of enantio-enriched all trans-3,4-dibenzyloxyl-5-benzyloxymethyl-2-pyrrolidinone 13a was developed based on SmI2-mediated benzyloxymethylation of O,O'-dibenzyltartarimide. The versatility of 13a and its antipode as the key building blocks for the asymmetric synthesis of pyrrolidine azasugars and homoazasugars has been demonstrated by elaborating them into naturally occurring DAB 1 (1), LAB 1 (2), N-hydroxyethyl-DAB 1 (4), 6-deoxy-DMDP 7, and 5-epi-radicamine B 36 as well as the reductive ring-opening product 35. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.02.087

文献信息

• Sugar-derived cyclic imines: one-pot synthesis and direct functionalization
  作者：Piotr Szcześniak、Sebastian Stecko、Olga Staszewska-Krajewska、Bartłomiej Furman

  DOI：10.1016/j.tet.2014.01.039

  日期：2014.3

  A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines. (C) 2014 Elsevier Ltd. All rights