(2R,4R)-1-benzyloxycarbonyl-4-hydroxy-2-(1,2:3,4-di-O-isopropylidene-α-D-galactopentopyranos-5-yl)pyrrolidine | 874341-17-0

• 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,4R)-1-benzyloxycarbonyl-4-hydroxy-2-(1,2:3,4-di-O-isopropylidene-α-D-galactopentopyranos-5-yl)pyrrolidine
• 英文别名: 6,7,9-trideoxy-6,9-(N-benzyloxycarbonylimino)-1,2:3,4-di-O-isopropylidene-8(R)-hydroxy-β-L-threo-D-galacto-non-1,5-pyranose；benzyl (2R,4R)-4-hydroxy-2-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]pyrrolidine-1-carboxylate
• CAS: 874341-17-0
• 化学式: C₂₃H₃₁NO₈
• 分子量: 449.501
• InChiKey: UXFSYPORMTWFAY-VLPZOFFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1-benzyloxycarbonyl-4-hydroxy-2-(1,2:3,4-di-O-isopropylidene-α-D-galactopentopyranos-5-yl)pyrrolidine 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 (2R,6S,7R,8S,9R,9aR)-2,6,7,8,9-pentahydroxy-perhydro-4-azaazulene
  参考文献：
  名称：

  A short and highly stereoselective route to polyhydroxy-perhydroazaazulenes via a C-(d-galacto-pentopyranos-5-yl)isoxazolidine

  摘要：

  A short and efficient route to enantiomerically pure hexahydroxy- and pentahydroxy-perhydroazaazulenes, ring-homologues of castanospermine, starting from the sole isoxazolidine derivative obtained in the 1,3-dipolar cycloaddition of a D-galactose-derived nitrone and methyl acrylate, is established. The procedure allows both backbone and stereochemical modulation of the products by choice of the starting monosaccharide. Structural assignment was based on crystallographic analysis of the starting isoxazolidine and NMR techniques. The products were tested for inhibitory activity against several glycosidases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.023
• 作为产物：
  描述：

  氯甲酸苄酯 、 (2R,4R)-4-hydroxy-2-(1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranos-5-yl)pyrrolidine 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 以96%的产率得到(2R,4R)-1-benzyloxycarbonyl-4-hydroxy-2-(1,2:3,4-di-O-isopropylidene-α-D-galactopentopyranos-5-yl)pyrrolidine
  参考文献：
  名称：

  A short and highly stereoselective route to polyhydroxy-perhydroazaazulenes via a C-(d-galacto-pentopyranos-5-yl)isoxazolidine

  摘要：

  A short and efficient route to enantiomerically pure hexahydroxy- and pentahydroxy-perhydroazaazulenes, ring-homologues of castanospermine, starting from the sole isoxazolidine derivative obtained in the 1,3-dipolar cycloaddition of a D-galactose-derived nitrone and methyl acrylate, is established. The procedure allows both backbone and stereochemical modulation of the products by choice of the starting monosaccharide. Structural assignment was based on crystallographic analysis of the starting isoxazolidine and NMR techniques. The products were tested for inhibitory activity against several glycosidases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.023

文献信息

• 1,3-Dipolar cycloaddition reaction of a d-galactose derived nitrone with allyl alcohol: synthesis of polyhydroxylated perhydroazaazulene alkaloids
  作者：Omprakash P. Bande、Vrushali H. Jadhav、Vedavati G. Puranik、Dilip D. Dhavale

  DOI：10.1016/j.tetasy.2007.05.012

  日期：2007.6

  Diastereofacial intermolecular 1,3-dipolar cycloaddition of D-galactose derived nitrone with allyl alcohol followed by tosylation afforded, in a 1:1 ratio endo- and exo-isooxazolidines 4a and 4b with complete diastereoselectivity at the nitrone carbon. The N-O bond reductive cleavage and S(N)2 displacement afforded the pyrrolidine ring with a galactose appendage that on acetonide cleavage and reductive amino-cyclization afforded pentahydroxylated perhydroazaazulenes 1a and 1b. (C) 2007 Elsevier Ltd. All rights reserved.