2,3,5-tri-O-benzyl-α-L-arabinofuranose | 60933-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzyl-α-L-arabinofuranose
• 英文别名: 2,3,5-tri-O-benzyl-β-L-arabinofuranose；2,3,5-Tribenzyloxy-α-L-arabinofuranose；(2R,3R,4S,5S)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-ol
• CAS: 60933-69-9
• 化学式: C₂₆H₂₈O₅
• 分子量: 420.505
• InChiKey: NAQUAXSCBJPECG-QEGGNFSNSA-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：
  0.31
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-α-L-arabinofuranose 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3R,4S,5R)-1-Benzyl-3,4-bis-benzyloxy-5-(4-methoxy-benzyl)-pyrrolidin-2-one
  参考文献：
  名称：

  A Short Synthetic Approach to Enantiomerically Pure (-)-Anisomycin

  摘要：

  A convenient enantiomerically pure route to an antibiotic, natural (-)-anisomycin has been developed in a short number of steps by featuring the stereocontrolled elaboration of the functionalized homochiral lactam derived from 2,3,5-tri-O-benzyl-beta-L-arabinofuranose involving no separation of stereoisomers through the entire sequence.

  DOI：

  10.3987/com-95-7214
• 作为产物：
  描述：

  2,3,5-三-O-苄基-L-呋喃阿拉伯糖 在 吡啶 作用下， 生成 2,3,5-tri-O-benzyl-α-L-arabinofuranose
  参考文献：
  名称：

  Syntheses with Partially Benzylated Sugars. II.¹ The Anomeric 1-O-Benzoyl-L-arabinopyranoses and 1-O-Benzoyl-L-arabinofuranoses and Their Tendencies to Undergo Acyl Migration

  摘要：

  DOI：

  10.1021/jo01046a015

文献信息

• Chiral Pyrroline-Based Ugi-Three-Component Reactions Are under Kinetic Control
  作者：Erwin R. van Rijssel、Theodorus P. M. Goumans、Gerrit Lodder、Herman S. Overkleeft、Gijsbert A. van der Marel、Jeroen D. C. Codée

  DOI：10.1021/ol4012053

  日期：2013.6.21

  is often assumed that the stereochemistry in Ugi multicomponent reactions is determined in the final Mumm rearrangement step, experimental and computational evidence that Ugi reactions on hydroxylated pyrrolines proceed under kinetic control is reported. The stereochemistry of the reaction is established with the addition of the isocyanide to the intermediate iminium ion, whose conformation is determined

  尽管通常认为Ugi多组分反应中的立体化学是在最后的Mumm重排步骤中确定的，但据报道实验和计算证据表明在动力学控制下Ugi在羟基化吡咯啉上的反应正在进行。反应的立体化学是通过将异氰酸酯加到中间体亚胺离子上来建立的，该亚胺离子的构象由其取代模式决定。
• Syntheses with Partially Benzylated Sugars. II.¹ The Anomeric 1-O-Benzoyl-L-arabinopyranoses and 1-O-Benzoyl-L-arabinofuranoses and Their Tendencies to Undergo Acyl Migration
  作者：Setsuzo Tejima、Hewitt G. Fletcher

  DOI：10.1021/jo01046a015

  日期：1963.11
• A Short Synthetic Approach to Enantiomerically Pure (-)-Anisomycin
  作者：Hidemi Yoda、Tomohito Nakajima、Hiroyasu Yamazaki、Kunihiko Takabe

  DOI：10.3987/com-95-7214

  日期：——

  A convenient enantiomerically pure route to an antibiotic, natural (-)-anisomycin has been developed in a short number of steps by featuring the stereocontrolled elaboration of the functionalized homochiral lactam derived from 2,3,5-tri-O-benzyl-beta-L-arabinofuranose involving no separation of stereoisomers through the entire sequence.