(Z)-5,6,7,8,9,10,11,12-octadeoxy-2,3-O-isopropylidene-D-ribo-dodec-6-enofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-5,6,7,8,9,10,11,12-octadeoxy-2,3-O-isopropylidene-D-ribo-dodec-6-enofuranose
• 英文别名: 2,3-O-isopropylidene-6(Z)-dodecene-L-ribofuranose；(3aR,6R,6aR)-2,2-dimethyl-6-[(Z)-oct-2-enyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: MQGCESJSRUUBBG-RALNIIQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-5,6,7,8,9,10,11,12-octadeoxy-2,3-O-isopropylidene-D-ribo-dodec-6-enofuranose 在 六甲基磷酰三胺 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 methyl 10(S),11(R),12(R)-trihydroxyeicosa-5(Z),8(Z),14(Z)-trienoate
  参考文献：
  名称：

  A concise synthesis of the methyl esters of (10S)-hepoxilin B3 and (10S)-trioxilin B3

  摘要：

  2,3:4,5-Di-O-Isopropylidene-D-mannose was converted to lactol 2,3-O-isopropylidene-6(Z)-dodecene-L-ribofuranose (6) by Grignard addition with propargyl magnesium bromide, alkylation of the resulting terminal alkyne, partial hydrogenation of the triple bond, and finally chemoselective cleavage of the 1,2-O-isopropylidene and subsequent periodate cleavage of the glycol. Wittig olefination of 6 led to methyl 10(S),11(R)-O-isopropylidene-10,11,12(R)-trihydroxyeicosa-5,8,14(Z)-trienoate (5), which could be converted to (10S)-trioxilin B3 methyl ester (3) in one step or to (10S)-hepoxilin B3 methyl ester (4) in three steps.

  DOI：

  10.1021/jo00062a017
• 作为产物：
  描述：

  mannitol triacetonide 在 Lindlar's catalyst 、 palladium on calcium fluoride poisoned with lead 六甲基磷酰三胺 、 正丁基锂 、 氢气 、 potassium carbonate 、 高碘酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 生成 (Z)-5,6,7,8,9,10,11,12-octadeoxy-2,3-O-isopropylidene-D-ribo-dodec-6-enofuranose
  参考文献：
  名称：

  Formal syntheses of hepoxilin B3, trioxilin B3 and substances against rice blast disease from D-mannitol

  摘要：

  标题化合物的制备中，一对差向异构的关键中间体可通过选择性断裂缩酮和乳醇形成诱导的差向异构化，从1,2:3,4:5,6-三-O-异丙叉-D-甘露醇中轻易获得。

  DOI：

  10.1039/c39930000821

文献信息

• Formal syntheses of hepoxilin B3, trioxilin B3 and substances against rice blast disease from D-mannitol
  作者：Wen-Lian Wu、Yu-Lin Wu

  DOI：10.1039/c39930000821

  日期：——

  A pair of epimeric key intermediates for preparation of the title compounds are readily available from 1,2 : 3,4 : 5,6-tri-O-isopropylidene-D-mannitol via selective cleavage of acetonide and lactol-formation-induced epimerization.

  标题化合物的制备中，一对差向异构的关键中间体可通过选择性断裂缩酮和乳醇形成诱导的差向异构化，从1,2:3,4:5,6-三-O-异丙叉-D-甘露醇中轻易获得。
• Chemoselective hydrolysis of terminal isopropylidene acetals and subsequent glycol cleavage by periodic acid in one pot
  作者：Wenlian Wu、Yulin Wu

  DOI：10.1021/jo00065a025

  日期：1993.6
• Wu, Wen-Lian; Wu, Yu-Lin, Journal of the Chemical Society. Perkin transactions I, 1993, # 24, p. 3081 - 3086
  作者：Wu, Wen-Lian、Wu, Yu-Lin

  DOI：——

  日期：——
• A concise synthesis of the methyl esters of (10S)-hepoxilin B3 and (10S)-trioxilin B3
  作者：Wenlian Wu、Yulin Wu

  DOI：10.1021/jo00062a017

  日期：1993.5

  2,3:4,5-Di-O-Isopropylidene-D-mannose was converted to lactol 2,3-O-isopropylidene-6(Z)-dodecene-L-ribofuranose (6) by Grignard addition with propargyl magnesium bromide, alkylation of the resulting terminal alkyne, partial hydrogenation of the triple bond, and finally chemoselective cleavage of the 1,2-O-isopropylidene and subsequent periodate cleavage of the glycol. Wittig olefination of 6 led to methyl 10(S),11(R)-O-isopropylidene-10,11,12(R)-trihydroxyeicosa-5,8,14(Z)-trienoate (5), which could be converted to (10S)-trioxilin B3 methyl ester (3) in one step or to (10S)-hepoxilin B3 methyl ester (4) in three steps.