[(1S)-1-[(2S,3R,4R)-4-azido-3-[tert-butyl(dimethyl)silyl]oxy-5-oxooxolan-2-yl]-2-[tert-butyl(dimethyl)silyl]oxyethyl] trifluoromethanesulfonate | 213457-96-6

• 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: [(1S)-1-[(2S,3R,4R)-4-azido-3-[tert-butyl(dimethyl)silyl]oxy-5-oxooxolan-2-yl]-2-[tert-butyl(dimethyl)silyl]oxyethyl] trifluoromethanesulfonate
• CAS: 213457-96-6
• 化学式: C₁₉H₃₆F₃N₃O₇SSi₂
• 分子量: 563.743
• InChiKey: FFMOPDHUVDPWSQ-GBJTYRQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(1S)-1-[(2S,3R,4R)-4-azido-3-[tert-butyl(dimethyl)silyl]oxy-5-oxooxolan-2-yl]-2-[tert-butyl(dimethyl)silyl]oxyethyl] trifluoromethanesulfonate 在 钯 盐酸 、 氢气 、 sodium acetate 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 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：

  (3R,4R,5R)-3-azido-4-((tert-butyldimethylsilyl)oxy)-5-((S)-1,2-dihydroxyethyl)dihydrofuran-2(3H)-one 在 吡啶 、 咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(1S)-1-[(2S,3R,4R)-4-azido-3-[tert-butyl(dimethyl)silyl]oxy-5-oxooxolan-2-yl]-2-[tert-butyl(dimethyl)silyl]oxyethyl] trifluoromethanesulfonate
  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

文献信息

• 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.