(2E,6E)-(10S,11R)-10,11-bis(methoxymethoxy)-2,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,6,14-triene | 122554-84-1

• 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: (2E,6E)-(10S,11R)-10,11-bis(methoxymethoxy)-2,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,6,14-triene
• 英文别名: [(2E,6E,10S,11R)-10,11-bis(methoxymethoxy)-2,7,11,15-tetramethylhexadeca-2,6,14-trienyl]sulfanylbenzene
• CAS: 122554-84-1
• 化学式: C₃₀H₄₈O₄S
• 分子量: 504.775
• InChiKey: AKIGMZLTTXUHCY-BGJRYDMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  35
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,6E)-(10S,11R)-10,11-bis(methoxymethoxy)-2,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,6,14-triene 在 正丁基锂 、 四甲基乙二胺 、 sodium 作用下， 以 异丙醇 为溶剂， 生成 (10E,14E)-(6S,7R,18S,19R)-6,18,19-tris(methoxymethoxy)-2,6,10,15,19,23-hexamethyltetracosa-2,10,14,22-tetraen-7-ol
  参考文献：
  名称：

  A short step synthesis of teurilene. Stereocontrolled sequential double cyclization of the C30-tetraenetetraol to the tandem tetrahydrofuran system

  摘要：

  DOI：

  10.1016/s0040-4039(00)82236-4
• 作为产物：
  描述：

  Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester 在 四氯化碳 、 4-二甲氨基吡啶 、 正丁基锂 、 四甲基乙二胺 、 氨 、 sodium 、 lithium 、 potassium carbonate 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 91.84h， 生成 (2E,6E)-(10S,11R)-10,11-bis(methoxymethoxy)-2,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,6,14-triene
  参考文献：
  名称：

  Total synthesis of the meso-triterpene polyether teurilene

  摘要：

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.

  DOI：

  10.1021/jo00007a013

文献信息

• HASHIMOTO, MASARU;HARIGAYA, HIROKO;YANAGIYA, MITSUTOSHI;SHIRAHAMA, HARUHI+, J. ORG. CHEM., 56,(1991) N, C. 2299-2311
  作者：HASHIMOTO, MASARU、HARIGAYA, HIROKO、YANAGIYA, MITSUTOSHI、SHIRAHAMA, HARUHI+

  DOI：——

  日期：——
• Total synthesis of the meso-triterpene polyether teurilene
  作者：Masaru Hashimoto、Hiroko Harigaya、Mitsutoshi Yanagiya、Haruhisa Shirahama

  DOI：10.1021/jo00007a013

  日期：1991.3

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.
• A short step synthesis of teurilene. Stereocontrolled sequential double cyclization of the C30-tetraenetetraol to the tandem tetrahydrofuran system
  作者：Masaru Hashimoto、Hiroko Harigaya、Mitsutoshi Yanagiya、Haruhisa Shirahama

  DOI：10.1016/s0040-4039(00)82236-4

  日期：1988.1