(3S,4R,5S)-3-azido-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxyoxolan-2-one | 213457-90-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,4R,5S)-3-azido-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxyoxolan-2-one
• CAS: 213457-90-0
• 化学式: C₆H₉N₃O₅
• 分子量: 203.155
• InChiKey: WPTGEMUDGDGUKP-KKQCNMDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-3-azido-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxyoxolan-2-one 在 钯 吡啶 、 咪唑 、 camphor-10-sulfonic acid 、 水 、 氢气 、 sodium acetate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,4S,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-oxa-5-azabicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Potential intermediates for incorporation of polyhydroxylated prolines into combinatorial libraries

  摘要：

  Bicyclic 2 and monocyclic 6 2-amino-1,4-lactones provide divergent intermediates for subsequent incorporation of polyhydroxylated prolines into combinatorial amide libraries. The X-ray crystal structure of an azidolactone, combined with molecular modelling, rationalises the very different behaviour of two azidolactones which are epimeric at a remote side-chain carbon. The conversion of 2 and 6 into DGDP 4 secures the structural claims in the paper. The enantiomers of 2 and 6 may provide access to libraries of potential inhibitors of UDP-Gal mutase and thus of mycobacterial cell wall biosynthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01256-8
• 作为产物：
  描述：

  methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate 在 水 、 三氟乙酸 作用下， 以96%的产率得到(3S,4R,5S)-3-azido-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxyoxolan-2-one
  参考文献：
  名称：

  Potential intermediates for incorporation of polyhydroxylated prolines into combinatorial libraries

  摘要：

  Bicyclic 2 and monocyclic 6 2-amino-1,4-lactones provide divergent intermediates for subsequent incorporation of polyhydroxylated prolines into combinatorial amide libraries. The X-ray crystal structure of an azidolactone, combined with molecular modelling, rationalises the very different behaviour of two azidolactones which are epimeric at a remote side-chain carbon. The conversion of 2 and 6 into DGDP 4 secures the structural claims in the paper. The enantiomers of 2 and 6 may provide access to libraries of potential inhibitors of UDP-Gal mutase and thus of mycobacterial cell wall biosynthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01256-8