Methyl (3S,4S,5R,6E,8E,10E)-3,5-dihydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoate | 139631-22-4

• 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: Methyl (3S,4S,5R,6E,8E,10E)-3,5-dihydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoate
• 英文别名: methyl (3S,4S,5R,6E,8E,10E)-3,5-dihydroxy-4,6,10-trimethyl-11-(2-methyl-1,3-oxazol-4-yl)undeca-6,8,10-trienoate
• CAS: 139631-22-4
• 化学式: C₁₉H₂₇NO₅
• 分子量: 349.427
• InChiKey: ZAYUJUBDNDQQOQ-XHSZWNCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl (3S,4S,5R,6E,8E,10E)-3,5-dihydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoate 在 咪唑 、 4-二甲氨基吡啶 、 lithium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 51.33h， 生成 (3S,4S,5R,6E,8E,10E)-3-((tert-Butyldimethylsilyl)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：

  2-甲基-4-恶唑甲酸乙酯 在 manganese(IV) oxide 、 sodium periodate 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二异丁基氢化铝 、 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 136.96h， 生成 Methyl (3S,4S,5R,6E,8E,10E)-3,5-dihydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoate
  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

文献信息

• Synthesis of the lower subunit of rhizoxin
  作者：Dale L. Boger、Timothy T. Curran

  DOI：10.1021/jo00034a010

  日期：1992.4

  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.