methyl (2R,3R,5R)-2-benzyl-3-(1,2:3,4-di-O-isopropylidene-α-D-galactopentopyranos-5-yl)isoxazolidine-5-carboxylate | 649571-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl (2R,3R,5R)-2-benzyl-3-(1,2:3,4-di-O-isopropylidene-α-D-galactopentopyranos-5-yl)isoxazolidine-5-carboxylate
• 英文别名: 4-[(3R,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose；methyl (3R,5R)-2-benzyl-3-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]-1,2-oxazolidine-5-carboxylate
• CAS: 649571-85-7
• 化学式: C₂₃H₃₁NO₈
• 分子量: 449.501
• InChiKey: AEPMFFHKUWOCQV-IWAFHXCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R,5R)-2-benzyl-3-(1,2:3,4-di-O-isopropylidene-α-D-galactopentopyranos-5-yl)isoxazolidine-5-carboxylate 在 咪唑 、 4-二甲氨基吡啶 、 氨 、 水 、 lithium 、 三乙基硼氢化锂 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 5-[(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)-2-hydroxy-5-pyrrolidinyl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose
  参考文献：
  名称：

  1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines

  摘要：

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.027
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 (Z)-N-benzyl-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-ylidene)amine N-oxide 以 甲苯 为溶剂， 以71%的产率得到methyl (2R,3R,5R)-2-benzyl-3-(1,2:3,4-di-O-isopropylidene-α-D-galactopentopyranos-5-yl)isoxazolidine-5-carboxylate
  参考文献：
  名称：

  由d-半乳糖和d-葡萄糖立体选择性合成3-糖基-5-甲氧基羰基-异恶唑烷

  摘要：

  据报道，丙烯酸甲酯的区域和立体选择性环加成反应衍生自d-半乳糖和d-葡萄糖的C-糖基硝酮，得到5-甲氧基羰基-3-（戊糖5-基或戊醇-1-基）异恶唑烷。实现了其中之一向4-羟基-2-（五糖基-5-基）吡咯烷衍生物的转化，该衍生物可能在制备多羟基-过氢氮杂azazulenes的途径中有用。

  DOI：

  10.1016/j.tetlet.2004.04.161

文献信息

• Stereoselective synthesis of 3-glycosyl-5-methoxycarbonyl-isoxazolidines from d-galactose and d-glucose
  作者：Pastora Borrachero、Francisca Cabrera-Escribano、Manuel Gómez-Guillén、Ma Isabel Torres

  DOI：10.1016/j.tetlet.2004.04.161

  日期：2004.6

  Regio- and stereoselective cycloaddition of methyl acrylate to C-glycosyl nitrones derived from d-galactose and d-glucose, giving 5-methoxycarbonyl-3-(pentoglycos-5-yl or pentitol-1-yl)isoxazolidines, is reported. Transformation of one of them into a 4-hydroxy-2-(pentoglycos-5-yl)pyrrolidine derivative, potentially useful in a route to polyhydroxy-perhydroazaazulenes, was achieved.

  据报道，丙烯酸甲酯的区域和立体选择性环加成反应衍生自d-半乳糖和d-葡萄糖的C-糖基硝酮，得到5-甲氧基羰基-3-（戊糖5-基或戊醇-1-基）异恶唑烷。实现了其中之一向4-羟基-2-（五糖基-5-基）吡咯烷衍生物的转化，该衍生物可能在制备多羟基-过氢氮杂azazulenes的途径中有用。
• A short and highly stereoselective route to polyhydroxy-perhydroazaazulenes via a C-(d-galacto-pentopyranos-5-yl)isoxazolidine
  作者：Ma Isabel Torres-Sánchez、Pastora Borrachero、Francisca Cabrera-Escribano、Manuel Gómez-Guillén、Manuel Angulo-Álvarez、Ma Jesús Diánez、Ma Dolores Estrada、Amparo López-Castro、Simeón Pérez-Garrido

  DOI：10.1016/j.tetasy.2005.10.023

  日期：2005.11

  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.
• 1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines
  作者：Pedro Merino、Santiago Franco、Francisco L. Merchan、Pilar Romero、Tomas Tejero、Santiago Uriel

  DOI：10.1016/j.tetasy.2003.08.027

  日期：2003.11

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.