Methanesulfonic acid (R)-{(4S,5R)-5-[(R)-1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester | 194918-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanesulfonic acid (R)-{(4S,5R)-5-[(R)-1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester
• CAS: 194918-20-2
• 化学式: C₂₂H₄₃N₃O₁₁S₂Si
• 分子量: 617.814
• InChiKey: VTRHGYZNCDVYRI-SGYMCOKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  181.65
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (R)-{(4S,5R)-5-[(R)-1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 在 水 、 三氟乙酸 作用下， 以90%的产率得到Methanesulfonic acid (1R,2S,3R,4R)-4-azido-1-((1S,2S)-1,2-dihydroxy-3-methanesulfonyloxy-propyl)-2,3,5-trihydroxy-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
• 作为产物：
  描述：

  (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 在 吡啶 、 4-二甲氨基吡啶 、 锂硼氢 、 sodium azide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methanesulfonic acid (R)-{(4S,5R)-5-[(R)-1-azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl 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