(1S,2S,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-en-1-ol | 916599-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-en-1-ol
• 英文别名: (1S,2S,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-1-[5-[[tert-butyl(dimethyl)silyl]oxymethyl]furan-2-yl]-2-methyl-4,5-bis(phenylmethoxy)hept-6-en-1-ol
• CAS: 916599-84-3
• 化学式: C₃₉H₆₀O₆Si₂
• 分子量: 681.073
• InChiKey: JASQIKBSYJKDQO-TUWRDAKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.22
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-en-1-ol 在 吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 bis(acetylacetonate)oxovanadium 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 Acetic acid (S)-6-[(1S,2R,3R,4R)-3,4-bis-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-hex-5-enyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester
  参考文献：
  名称：

  Studies on Oxidopyrylium [5 + 2] Cycloadditions:  Toward a General Synthetic Route to the C12-Hydroxy Daphnetoxins

  摘要：

  [GRAPHICS]12-Hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on D-ribose. Depending on the choice of protecting groups and solvent, the oxidopyrylium-alkene [5+2] cycloaddition originating from A provides cycloadduct diastereomer B or C with good to excellent selectivity.

  DOI：

  10.1021/ol062234e
• 作为产物：
  描述：

  (1S,2R,3R,4S,5R)-1-[5-[[tert-butyl(dimethyl)silyl]oxymethyl]furan-2-yl]-2-methyl-4,5-bis(phenylmethoxy)hept-6-ene-1,3-diol 在 2,6-二甲基吡啶 、 柠檬酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.58h， 生成 (1S,2S,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-en-1-ol
  参考文献：
  名称：

  Studies on Oxidopyrylium [5 + 2] Cycloadditions:  Toward a General Synthetic Route to the C12-Hydroxy Daphnetoxins

  摘要：

  [GRAPHICS]12-Hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on D-ribose. Depending on the choice of protecting groups and solvent, the oxidopyrylium-alkene [5+2] cycloaddition originating from A provides cycloadduct diastereomer B or C with good to excellent selectivity.

  DOI：

  10.1021/ol062234e

文献信息

• Studies on Oxidopyrylium [5 + 2] Cycloadditions:  Toward a General Synthetic Route to the C12-Hydroxy Daphnetoxins
  作者：Paul A. Wender、F. Christopher Bi、Nicole Buschmann、Francis Gosselin、Cindy Kan、Jung-Min Kee、Hirofumi Ohmura

  DOI：10.1021/ol062234e

  日期：2006.11.9

  [GRAPHICS]12-Hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on D-ribose. Depending on the choice of protecting groups and solvent, the oxidopyrylium-alkene [5+2] cycloaddition originating from A provides cycloadduct diastereomer B or C with good to excellent selectivity.