(5Z,8Z)-9-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-non-3-enyl]-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester | 1053615-64-7

• 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: (5Z,8Z)-9-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-non-3-enyl]-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester
• 英文别名: methyl (5Z,8Z)-9-[(4S,5S)-2,2-dimethyl-5-[(Z,1R)-1-(4-methylphenyl)sulfonyloxynon-3-enyl]-1,3-dioxolan-4-yl]nona-5,8-dienoate
• CAS: 1053615-64-7
• 化学式: C₃₁H₄₆O₇S
• 分子量: 562.768
• InChiKey: YCPJGHQIXUMCMK-PHUQWBIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5Z,8Z)-9-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-non-3-enyl]-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester 在 potassium carbonate 、 对甲苯磺酸 作用下， 生成 methyl 10(S)-hydroxy-11(S),12(S)-epoxyeicosa-5,8,14(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：

  (6R)-1,2:4,5-di-O-isopropylidene-8-tetradecyne-D-glycero-D-manno-1,2,3,4,5,6-hexol 在 Lindlar's catalyst 吡啶 、 喹啉 、 六甲基磷酰三胺 、 氢气 、 双(三甲基硅烷基)氨基钾 、 高碘酸 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， -20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 (5Z,8Z)-9-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-non-3-enyl]-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester
  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

文献信息

• 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.