(3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)pyrrolidine-2,5-dione | 321566-90-9

• 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: (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)pyrrolidine-2,5-dione
• 英文别名: (3R,4R)-1-[(4-methoxyphenyl)methyl]-3,4-bis(phenylmethoxy)pyrrolidine-2,5-dione
• CAS: 321566-90-9
• 化学式: C₂₆H₂₅NO₅
• 分子量: 431.488
• InChiKey: TUWRVONXMFNWDO-DNQXCXABSA-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：

  (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)pyrrolidine-2,5-dione 在 ammonium cerium (IV) nitrate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (3R,4R)-3,4-bis(benzyloxy)-1-(but-3-enyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  宝石-二氟亚甲基化的二羟基吡咯烷酮和吲哚并咪唑的不对称合成

  摘要：

  描述了宝石-二氟亚甲基化的二羟基吡咯烷核苷和吲哚并核苷的不对称合成。氟化物催化的亲核加成PhSCF的2森达3（1）手性酰亚胺在令人满意的产率实现，以提供的混合物顺式-和反-异构体6 - 9与中度至良好非对映选择性。的苯硫基团的还原裂解，随后通过分子内自由基环化顺式-异构体6 - 9发生下回流条件，得到相应的宝石-difluoromethylenated 1-氮杂双环化合物10 - 13在中等产率作为一个可分离混合物的顺式-和反式-异构体。所述顺式化合物的异构体10和12以及反式- 13被容易地转化为宝石-difluoromethylenated dihydroxypyrrolizidines 20和27和吲哚里28分别由羟基和有机金属加成，接着通过氢的还原裂解。

  DOI：

  10.1021/jo301327s
• 作为产物：
  描述：

  4-甲氧基苄胺 在 silver(l) oxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙酸乙酯 为溶剂， 反应 96.0h， 生成 (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)pyrrolidine-2,5-dione
  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

文献信息

• Synthesis of Polyhydroxylated Quinolizidine and Indolizidine Scaffolds from Sugar-Derived Lactams via a One-Pot Reduction/Mannich/Michael Sequence
  作者：Piotr Szcześniak、Sebastian Stecko、Elżbieta Maziarz、Olga Staszewska-Krajewska、Bartłomiej Furman

  DOI：10.1021/jo502146z

  日期：2014.11.7

  A direct approach to the synthesis of indolizidine and quinolizidine scaffolds of iminosugars is described. The presented strategy is based on a one-pot sugar lactam reduction with Schwartz’s reagent followed by a diastereoselective Mannich/Michael tandem reaction of the resulting sugar imine with Danishefsky’s diene. The stereochemical course of the investigated reaction has been explained in detail

  描述了一种直接合成亚氨基糖的吲哚并立定和喹喔嗪骨架的方法。提出的策略是基于先用Schwartz试剂还原一锅糖内酰胺，然后再将得到的糖亚胺与Danishefsky的二烯进行非对映选择性的Mannich / Michael串联反应。已详细解释了所研究反应的立体化学过程。所获得的双环产物是用于合成各种天然存在的多羟基化生物碱及其衍生物的有吸引力的结构单元。
• Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated <i>N</i>,<i>O</i>-Acetals Derived from <scp>l</scp>-Tartaric Acid
  作者：Abdelkhalek Ben Jamaa、Fabienne Grellepois

  DOI：10.1021/acs.joc.7b01814

  日期：2017.10.6

  substituent, cyclic α-trifluoromethylated N-acyliminium ions were successfully generated from fluorinated O-acetyl-N,O-acetal l-tartaric acid derivatives. The addition of nitriles on these intermediates occurred with high to excellent syn diastereoselectivity and led, in most cases, to oxazolines and amides as single diastereomers. The diastereoselectivity of the addition and the nature of the reaction product

  尽管存在高度吸电子的氟化取代基，但还是从氟化的O-乙酰基N，O-乙缩醛1-酒石酸衍生物成功生成了环状α-三氟甲基化的N-酰基亚胺离子。在这些中间体上以高至极高的合成力添加腈非对映选择性，并在大多数情况下导致恶唑啉和酰胺为单一非对映异构体。添加的非对映选择性和反应产物的性质取决于酒石酸支架的羟基上的取代基。该方法获得了对映纯的，高度官能化的5-（三氟甲基）吡咯烷-2-酮衍生物，其在四取代的碳上带有氟化取代基。
• 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.