(3S,4R,5R)-5-benzyloxymethyl-3,4-dibenzyloxy-1-(4-methoxybenzyl)-pyrrolidin-2-one | 944543-93-5

• 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: (3S,4R,5R)-5-benzyloxymethyl-3,4-dibenzyloxy-1-(4-methoxybenzyl)-pyrrolidin-2-one
• 英文别名: N-4-methoxybenzyl-2,3,5-tri-O-benzyl-D-arabino-γ-lactam；(3S,4R,5R)-1-[(4-methoxyphenyl)methyl]-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidin-2-one
• CAS: 944543-93-5
• 化学式: C₃₄H₃₅NO₅
• 分子量: 537.656
• InChiKey: ZOVSQGWORQVENA-SLGZMBILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-5-benzyloxymethyl-3,4-dibenzyloxy-1-(4-methoxybenzyl)-pyrrolidin-2-one 在 lithium aluminium tetrahydride 、 ammonium cerium (IV) nitrate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 13.0h， 生成 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-D-arabinitol
  参考文献：
  名称：

  Design and Pharmacological Chaperone Effects of N-(4′-Phenylbutyl)-DAB Derivatives Targeting the Lipophilic Pocket of Lysosomal Acid α-Glucosidase

  摘要：

  DOI：

  10.1021/acs.jmedchem.3c00637
• 作为产物：
  描述：

  L-O,O-dibenzyltartaric acid 在 三乙基硅烷 、 三氟化硼乙醚 、 magnesium 、 乙酰氯 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (3S,4R,5R)-5-benzyloxymethyl-3,4-dibenzyloxy-1-(4-methoxybenzyl)-pyrrolidin-2-one
  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

• Arabinoamidine synthesis and its inhibition toward β-glucosidase (sweet almonds) in comparison to a library of galactonoamidines
  作者：Jessica B. Pickens、Susanne Striegler、Qiu-Hua Fan

  DOI：10.1016/j.bmc.2016.04.069

  日期：2016.8

  hydrolysis-promoting amino acids in the active site and inhibits the enzymatic hydrolysis of beta-glucosides in the low nanomolar concentration range. While both inhibitors are competitive, their inhibition ability is more than 37,000-fold different.

  针对β-葡糖苷酶的有效抑制剂的发展，研究了一个类似的半乳糖醛am库和一个阿拉伯糖idine作为甜杏仁β-葡糖苷酶的抑制剂。已显示阿拉伯ino中的五元糖苷在保留酶的活性位点与质子供体相互作用，但不与亲核试剂相互作用。相比之下，具有六元糖苷和相同糖苷配基的相应的半乳糖o与活性位点中的两个水解促进氨基酸相互作用，并在低纳摩尔浓度范围内抑制β-葡萄糖苷的酶促水解。尽管两种抑制剂都具有竞争性，但它们的抑制能力却相差37,000倍以上。
• A concise and divergent approach to radicamine B and hyacinthacine A3 based on a step-economic transformation
  作者：Jin-Cheng Liao、Kai-Jiong Xiao、Xiao Zheng、Pei-Qiang Huang

  DOI：10.1016/j.tet.2012.01.085

  日期：2012.7

  Based on our recently developed step-economic methodology of reductive alkylation of lactams/amides, we have developed a two-step synthesis of azasugar radicamine B (2a) and a four-step synthesis of azasugar hyacinthacine A(3) (5) from the common chiral building block 12. Hantzsch ester (HEH) was used as a milder hydride donor in the one-pot stereoselective reductive alkylation of lactam 12. The Wacker oxidation of fully substituted pyrrolidine derivative 2,5-trans-17 led to the synthesis of hyacinthacine A(3) (5). Compound 2,5-trans-17 could also serve as a plausible key intermediate for the synthesis of broussonetine sub-class of azasugars. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.
• 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