Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(1S,2S)-2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-hydroxy-1-methyl-ethyl}-pent-4-enyl ester | 916600-03-8

• 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: Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(1S,2S)-2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-hydroxy-1-methyl-ethyl}-pent-4-enyl ester
• 英文别名: [(1S,2S,3R,4R,5R)-1-[5-[[tert-butyl(dimethyl)silyl]oxymethyl]furan-2-yl]-1-hydroxy-2-methyl-4,5-bis(phenylmethoxy)hept-6-en-3-yl] acetate
• CAS: 916600-03-8
• 化学式: C₃₅H₄₈O₇Si
• 分子量: 608.847
• InChiKey: XOUACEWUFHRYDA-QZVVKDSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.76
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(1S,2S)-2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-hydroxy-1-methyl-ethyl}-pent-4-enyl ester 在 吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 bis(acetylacetonate)oxovanadium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 Acetic acid (1S,2R,3R,4R,5R,6R,8R)-4,5-bis-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-11-oxo-12-oxa-tricyclo[6.3.1.0^1,6]dodec-9-en-3-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：

  (4R,5R)-4,5-bis(phenylmethoxy)hept-6-en-3-one 在 吡啶 、 4-二甲氨基吡啶 、 锂硼氢 、 氯代二环己基硼烷 、 三乙胺 、 柠檬酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 64.08h， 生成 Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(1S,2S)-2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-hydroxy-1-methyl-ethyl}-pent-4-enyl 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