(3S,4S)-1-(4-methoxybenzyl)-3,4-dibenzyloxy-2,5-pyrrolidinedione | 944543-96-8

• 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: (3S,4S)-1-(4-methoxybenzyl)-3,4-dibenzyloxy-2,5-pyrrolidinedione
• 英文别名: (3S,4S)-1-[(4-methoxyphenyl)methyl]-3,4-bis(phenylmethoxy)pyrrolidine-2,5-dione
• CAS: 944543-96-8
• 化学式: C₂₆H₂₅NO₅
• 分子量: 431.488
• InChiKey: TUWRVONXMFNWDO-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S)-1-(4-methoxybenzyl)-3,4-dibenzyloxy-2,5-pyrrolidinedione 在 三乙基硅烷 、 ammonium cerium(IV) nitrate 、 dimethylsulfide borane complex 、 三氟化硼乙醚 、 magnesium 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 12.5h， 生成 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-D-arabinitol
  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：

  (2S,3S)-diethyl 2,3-bis(phenylmethoxy)succinate 在 lithium hydroxide 、 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 (3S,4S)-1-(4-methoxybenzyl)-3,4-dibenzyloxy-2,5-pyrrolidinedione
  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

• A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide
  作者：Xiang Zhou、Wen-Jun Liu、Jian-Liang Ye、Pei-Qiang Huang

  DOI：10.1016/j.tet.2007.02.087

  日期：2007.7

  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.
• A study on the racemization step in the synthesis of pyrrolidinols via cyclic α-hydroxyimides
  作者：Jin-Li Zheng、Hui Liu、Yu-Feng Zhang、Wei Zhao、Jin-Shuan Tong、Yuan-Ping Ruan、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2011.01.012

  日期：2011.2

  Analytical HPLC methods for the determination of the enantiomeric excess of N-protected malimides 1 as well as the corresponding pyrrolidinol 5 and tartarimides 2 and 3 have been established. On this basis, a study to reveal the racemization step in the synthesis of pyrrolidinols from alpha-hydroxyacids, via chiral cyclic alpha-hydroxyimides, has been undertaken. It was confirmed that the known, one-step method for the synthesis of the N-protected chiral cyclic imides from alpha-hydroxydiacids proceeded with little racemization, and partial racemization has been proven to occur during the reduction of the resultant imide la with LAH to yield the corresponding pyrrolidinol 5. Conditions have been defined in order to avoid racemization in the LAH reduction step. (C) 2011 Elsevier Ltd. All rights reserved.
• Design and Pharmacological Chaperone Effects of <i>N</i>-(4′-Phenylbutyl)-DAB Derivatives Targeting the Lipophilic Pocket of Lysosomal Acid α-Glucosidase
  作者：Atsushi Kato、Izumi Nakagome、Maki Kise、Kousuke Yoshimura、Nobutada Tanaka、Robert J. Nash、George W. J. Fleet、Yota Kobayashi、Hayato Ikeda、Takuya Okada、Naoki Toyooka

  DOI：10.1021/acs.jmedchem.3c00637

  日期：2023.7.13