(6E,8E,10E)-(3S,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6,10-trimethyl-11-(2-methyl-oxazol-4-yl)-undeca-6,8,10-trienoic acid | 139655-30-4

• 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: (6E,8E,10E)-(3S,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6,10-trimethyl-11-(2-methyl-oxazol-4-yl)-undeca-6,8,10-trienoic acid
• CAS: 139655-30-4
• 化学式: C₃₄H₄₃NO₅Si
• 分子量: 573.805
• InChiKey: YXRUHGWPVIDSHU-NTANHMEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.79
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (6E,8E,10E)-(3S,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6,10-trimethyl-11-(2-methyl-oxazol-4-yl)-undeca-6,8,10-trienoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以51%的产率得到(3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone
  参考文献：
  名称：

  Synthesis of the lower subunit of rhizoxin

  摘要：

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.

  DOI：

  10.1021/jo00034a010
• 作为产物：
  描述：

  Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside 在 sodium periodate 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 二异丁基氢化铝 作用下， 以 1,4-二氧六环 、 乙醚 、 正己烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 16.75h， 生成 (6E,8E,10E)-(3S,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6,10-trimethyl-11-(2-methyl-oxazol-4-yl)-undeca-6,8,10-trienoic acid
  参考文献：
  名称：

  Synthesis of the lower subunit of rhizoxin

  摘要：

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.

  DOI：

  10.1021/jo00034a010