1,2:4,5-di-O-isopropylidene-8(Z)-tetradecene-D-glycero-D-manno-1,2,3,4,5,6-hexol | 148565-79-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,2:4,5-di-O-isopropylidene-8(Z)-tetradecene-D-glycero-D-manno-1,2,3,4,5,6-hexol
• 英文别名: (Z,1R)-1-[(4R,5S)-5-[(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]non-3-en-1-ol
• CAS: 148565-79-1
• 化学式: C₂₀H₃₆O₆
• 分子量: 372.502
• InChiKey: KDBOUYOHYDPSDR-UTCAGISSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2:4,5-di-O-isopropylidene-8(Z)-tetradecene-D-glycero-D-manno-1,2,3,4,5,6-hexol 在 六甲基磷酰三胺 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 高碘酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 32.0h， 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：

  (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 喹啉 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以97%的产率得到1,2:4,5-di-O-isopropylidene-8(Z)-tetradecene-D-glycero-D-manno-1,2,3,4,5,6-hexol
  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

• 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
• 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.