Methanesulfonic acid (1R,2S,3R,4S)-4-azido-1-((1S,2S)-3-methanesulfonyloxy-1,2-bis-triethylsilanyloxy-propyl)-2,3,5-tris-triethylsilanyloxy-pentyl ester | 194918-16-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid (1R,2S,3R,4S)-4-azido-1-((1S,2S)-3-methanesulfonyloxy-1,2-bis-triethylsilanyloxy-propyl)-2,3,5-tris-triethylsilanyloxy-pentyl ester
• 英文别名: [(2S,3S,4R,5S,6R,7S)-7-azido-4-methylsulfonyloxy-2,3,5,6,8-pentakis(triethylsilyloxy)octyl] methanesulfonate
• CAS: 194918-16-6
• 化学式: C₄₀H₉₁N₃O₁₁S₂Si₅
• 分子量: 994.736
• InChiKey: VUXMMPGBBUGPGF-ONSKYXJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.57
• 重原子数：
  61
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  164
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (1R,2S,3R,4S)-4-azido-1-((1S,2S)-3-methanesulfonyloxy-1,2-bis-triethylsilanyloxy-propyl)-2,3,5-tris-triethylsilanyloxy-pentyl ester 在 氧化汞红 、 potassium carbonate 作用下， 以 丁酮 为溶剂， 以66%的产率得到(3aR,6R,6aR)-6-{(4S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one
  参考文献：
  名称：

  Synthesis of casuarines [pentahydroxylated pyrrolizidines] by sodium hydrogen telluride-induced cyclisations of azidodimesylates

  摘要：

  The key step in the synthesis of four diastereomers of casuarine from eight carbon sugar lactones is the efficient reduction of open chain azidodimesylates by sodium hydrogen telluride [Suzuki-Takaoka reduction] to allow the formation of the pyrrolizidine nucleus by bicyclisation. This is the first report of the synthesis of such highly oxygenated pyrrolizidines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01306-3
• 作为产物：
  描述：

  三乙基氯硅烷 、 7-azido-7-deoxy-1,4-di-O-methanesulphonyl-L-threo-L-talo-octitol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以45%的产率得到Methanesulfonic acid (1R,2S,3R,4S)-4-azido-1-((1S,2S)-3-methanesulfonyloxy-1,2-bis-triethylsilanyloxy-propyl)-2,3,5-tris-triethylsilanyloxy-pentyl ester
  参考文献：
  名称：

  Synthesis of casuarines [pentahydroxylated pyrrolizidines] by sodium hydrogen telluride-induced cyclisations of azidodimesylates

  摘要：

  The key step in the synthesis of four diastereomers of casuarine from eight carbon sugar lactones is the efficient reduction of open chain azidodimesylates by sodium hydrogen telluride [Suzuki-Takaoka reduction] to allow the formation of the pyrrolizidine nucleus by bicyclisation. This is the first report of the synthesis of such highly oxygenated pyrrolizidines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01306-3

文献信息

• Synthesis of casuarines [pentahydroxylated pyrrolizidines] by sodium hydrogen telluride-induced cyclisations of azidodimesylates
  作者：Andrew A. Bell、Lea Pickering、Alison A. Watson、Robert J. Nash、Yuan T. Pan、Alan D. Elbein、George W.J. Fleet

  DOI：10.1016/s0040-4039(97)01306-3

  日期：1997.8

  The key step in the synthesis of four diastereomers of casuarine from eight carbon sugar lactones is the efficient reduction of open chain azidodimesylates by sodium hydrogen telluride [Suzuki-Takaoka reduction] to allow the formation of the pyrrolizidine nucleus by bicyclisation. This is the first report of the synthesis of such highly oxygenated pyrrolizidines. (C) 1997 Elsevier Science Ltd.