4-guaiene-11-O-β-D-(3'-angeloxy-6'-deoxy)glucopyranoside | 41446-98-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-guaiene-11-O-β-D-(3'-angeloxy-6'-deoxy)glucopyranoside
• 英文别名: 2-[(5R,8S,8aS)-3,8-dimethyl-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]propan-2-ol；guaia-4(5)-en-11-ol；Isoguaiol
• CAS: 41446-98-4
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: QWMCMMDXNNGJGG-UHTWSYAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-guaiene-11-O-β-D-(3'-angeloxy-6'-deoxy)glucopyranoside 在 吡啶 、 叔丁基过氧化氢 、 selenium(IV) oxide 、 氯化亚砜 作用下， 以 癸烷 、 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 (4S,5S,8S,8aS)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,4,5,6,7,8,8a-octahydroazulen-4-ol
  参考文献：
  名称：

  Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-epi-Melicodenones C and E, and Other Guaiane-Type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol

  摘要：

  The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products guaia-4(5)-en-11-ol (2a), guaia-5(6)-en-11-ol (3), and aciphyllene (4a) and epimers of the recently isolated natural products, 1-epi-guaia-4(5)-en-11-ol (2b), 1-epi-aciphyllene (4b), and 1-epi-melicodenones C (5a) and E (6a), were synthesized in good yields in relatively few steps.

  DOI：

  10.1021/np500611z
• 作为产物：
  描述：

  (-)-愈创醇 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.5h， 生成 4-guaiene-11-O-β-D-(3'-angeloxy-6'-deoxy)glucopyranoside
  参考文献：
  名称：

  Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-epi-Melicodenones C and E, and Other Guaiane-Type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol

  摘要：

  The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products guaia-4(5)-en-11-ol (2a), guaia-5(6)-en-11-ol (3), and aciphyllene (4a) and epimers of the recently isolated natural products, 1-epi-guaia-4(5)-en-11-ol (2b), 1-epi-aciphyllene (4b), and 1-epi-melicodenones C (5a) and E (6a), were synthesized in good yields in relatively few steps.

  DOI：

  10.1021/np500611z

文献信息

• van der Gen,A. et al., Recueil des Travaux Chimiques des Pays-Bas, 1972, vol. 91, p. 1433 - 1440
  作者：van der Gen,A. et al.

  DOI：——

  日期：——
• Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-<i>epi</i>-Melicodenones C and E, and Other Guaiane-Type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol
  作者：An-Cheng Huang、Christopher J. Sumby、Edward R. T. Tiekink、Dennis K. Taylor

  DOI：10.1021/np500611z

  日期：2014.11.26

  The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products guaia-4(5)-en-11-ol (2a), guaia-5(6)-en-11-ol (3), and aciphyllene (4a) and epimers of the recently isolated natural products, 1-epi-guaia-4(5)-en-11-ol (2b), 1-epi-aciphyllene (4b), and 1-epi-melicodenones C (5a) and E (6a), were synthesized in good yields in relatively few steps.