5-O-tert-butyldiphenylsilyl-α-D-arabino-furanose | 915069-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-tert-butyldiphenylsilyl-α-D-arabino-furanose
• 英文别名: (2S,3S,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolane-2,3,4-triol
• CAS: 915069-72-6
• 化学式: C₂₁H₂₈O₅Si
• 分子量: 388.536
• InChiKey: UBTTVAWQIDVDNL-ZRNYENFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  D-arabinofuranose 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 5-O-tert-butyldiphenylsilyl-α-D-arabino-furanose 、 5-O-tert-butyldiphenylsilyl-β-D-arabino-furanose
  参考文献：
  名称：

  Deoxygenation at the C3 position of d- and l-arabinofuranose: stereospecific access to enantiomeric cordycepose derivatives

  摘要：

  Efficient synthesis of 3-deoxy-1,2-O-isopropylidene-beta-D- and beta-L-threo-pentofuranose (1,2-O-isopropylidene-beta-D- and beta-L-cordycepose) was accomplished starting from D- and L-arabinofuranose derivatives, respectively, by the action of LiBH(Et)(3) on corresponding intermediate 3-O-lyxofuranosyl trifluoromethanesulfonates. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.07.017

文献信息

• Carbohydrate chiral-pool approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates
  作者：Bogdan Doboszewski、Piet Herdewijn

  DOI：10.1016/j.tet.2008.03.088

  日期：2008.6

  D-Glucose, L-Xylose, and D- and L-arabinose were sources of chirality to obtain four enantiomerically pure 3-hydroxy-2-methylbutanoic acids, which were reacted with 2-naphthyldiazomethane to furnish their fluorescent 2-naphthylmethyl esters. (C) 2008 Elsevier Ltd. All rights reserved.