(3R,4R,5S)-3-azido-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxyoxolan-2-one | 179992-65-5

• 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: (3R,4R,5S)-3-azido-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxyoxolan-2-one
• CAS: 179992-65-5
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: XSXDPABALMSCLC-BDVNFPICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-3-azido-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxyoxolan-2-one 在 钯 吡啶 、 咪唑 、 盐酸 、 水 、 氢气 、 sodium acetate 、 三乙基硼氢化锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,5-二(羟基甲基)-3,4-吡咯烷二醇
  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：

  [(3S,4S,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-2-oxooxolan-3-yl] trifluoromethanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 以71%的产率得到(3R,4R,5S)-3-azido-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxyoxolan-2-one
  参考文献：
  名称：

  Kruelle, Thomas M.; Davis, Benjamin; Ardron, Helen, Journal of the Chemical Society. Chemical communications, 1996, # 11, p. 1271 - 1272

  摘要：

  DOI：

文献信息

• Kruelle, Thomas M.; Davis, Benjamin; Ardron, Helen, Journal of the Chemical Society. Chemical communications, 1996, # 11, p. 1271 - 1272
  作者：Kruelle, Thomas M.、Davis, Benjamin、Ardron, Helen、Long, Daniel D.、Hindle, Neil A.、et al.

  DOI：——

  日期：——
• Potential intermediates for incorporation of polyhydroxylated prolines into combinatorial libraries
  作者：Daniel D. Long、Signe M. Frederiksen、Daniel G. Marquess、Alexandra L. Lane、David J. Watkin、David A. Winkler、George W.J. Fleet

  DOI：10.1016/s0040-4039(98)01256-8

  日期：1998.8

  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.