(3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-2-one | 158349-27-0

• 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: (3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-2-one
• 英文别名: (3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidin-2-one
• CAS: 158349-27-0
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: QLYIRCPWSGOZMA-SDHSZQHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以94 %的产率得到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 、 ammonium cerium(IV) nitrate 、 三氟化硼乙醚 、 magnesium 、 乙酰氯 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 27.5h， 生成 (3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)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

• 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。
• 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 Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams
  作者：Piotr Szcześniak、Barbara Grzeszczyk、Bartłomiej Furman

  DOI：10.3390/molecules26185459

  日期：——

  An efficient method for the synthesis of nojirimycin- and pyrrolidine-based iminosugar derivatives has been developed. The strategy is based on the partial reduction in sugar-derived lactams by Schwartz’s reagent and tandem stereoselective nucleophilic addition of cyanide or a silyl enol ether dictated by Woerpel’s or diffusion control models, which affords amino-modified iminosugars, such as ADMDP

  已开发出一种合成野尻霉素和吡咯烷基亚氨基糖衍生物的有效方法。该策略基于 Schwartz 试剂部分还原糖衍生的内酰胺，以及 Woerpel 或扩散控制模型规定的氰化物或甲硅烷基烯醇醚的串联立体选择性亲核加成，提供氨基修饰的亚氨基糖，如 ADMDP 或更高的野尻霉素衍生物.
• Concise synthesis of bicyclic iminosugars <i>via</i> reductive functionalization of sugar-derived lactams and subsequent RCM reaction
  作者：Piotr Szcześniak、Bartłomiej Furman

  DOI：10.1039/d1ob01172c

  日期：——

  method for the synthesis of bicyclic iminosugars has been developed. The strategy is based on the partial reduction of sugar-derived lactams by Schwartz's reagent and tandem stereoselective nucleophile addition dictated by Woerpel's model which affords polyhydroxylated cyclic amines as key intermediates. Introduction of a vinyl or allyl group to the iminosugar produces diene derivatives that can be

  开发了一种合成双环亚氨基糖的有效方法。该策略基于通过 Schwartz 试剂和串联立体选择性亲核试剂加成的糖衍生内酰胺的部分还原，由 Woerpel 模型提供多羟基化环胺作为关键中间体。将乙烯基或烯丙基基团引入亚氨基糖产生二烯衍生物，该衍生物可以进行闭环复分解反应 (RCM)，以良好至极好的产率提供多羟基化吡咯里西啶、中氮茚和喹唑啉衍生物。该反应序列已应用于风信子 A 2的正式合成，它是一种多羟基化的吡咯里西啶生物碱。
• A facile transformation of sugar lactones to azasugars
  作者：Herman S. Overkleeft、Jim van Wiltenburg、Upendra K. Pandit

  DOI：10.1016/s0040-4020(01)86715-6

  日期：1994.4

  The synthesis of pyrano- and furano- sugar lactams from the corresponding lactones, in a five step sequence, is described.