2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose | 874460-57-8

• 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: 2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose
• CAS: 874460-57-8
• 化学式: C₁₆H₁₉N₃O₅
• 分子量: 333.344
• InChiKey: LITVTQPPGJZNEY-HGTKMLMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  102.75
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose 在 palladium on activated charcoal sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 氢气 作用下， 以 甲醇 、 乙醚 、 水 、 叔丁醇 为溶剂， 反应 3.33h， 生成 methyl (3-O-benzyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ulopyranosyl amine)onate
  参考文献：
  名称：

  Stereocontrolled synthesis of thiohydantoin spironucleosides from sugar spiroacetals

  摘要：

  5-Epithiohydantocidin, N-alkyl and N-glycosylthiohydantoin spironucleosides are prepared from glycosylaminoesters and from furanoid and pyranoid methyl isothiocyanatoulosonates. The aminoesters; and the isothiocyanates are obtained, in a stereocontrolled manner, from sugar spiroacetals through a high-yielding sequence involving ring opening with trimethyl azide, formation of an ester group, reduction of the azide, and, in the case of isothiocyanates, reaction with thiophosgene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.128
• 作为产物：
  描述：

  2-azido-3-O-benzyl-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以92%的产率得到2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  Stereocontrolled synthesis of thiohydantoin spironucleosides from sugar spiroacetals

  摘要：

  5-Epithiohydantocidin, N-alkyl and N-glycosylthiohydantoin spironucleosides are prepared from glycosylaminoesters and from furanoid and pyranoid methyl isothiocyanatoulosonates. The aminoesters; and the isothiocyanates are obtained, in a stereocontrolled manner, from sugar spiroacetals through a high-yielding sequence involving ring opening with trimethyl azide, formation of an ester group, reduction of the azide, and, in the case of isothiocyanates, reaction with thiophosgene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.128