(2R,5R)-2-<(E)-(S)-1-<(tert-butyldimethylsilyl)oxy>-5-methyl-6-(phenylthio)hex-4-enyl>tetrahydro-5-<(S)-1-(methoxymethoxy)-1,5-dimethylhex-4-enyl>-2-methylfuran | 121400-93-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R,5R)-2-<(E)-(S)-1-<(tert-butyldimethylsilyl)oxy>-5-methyl-6-(phenylthio)hex-4-enyl>tetrahydro-5-<(S)-1-(methoxymethoxy)-1,5-dimethylhex-4-enyl>-2-methylfuran
• 英文别名: tert-butyl-[(E,1S)-1-[(2R,5R)-5-[(2S)-2-(methoxymethoxy)-6-methylhept-5-en-2-yl]-2-methyloxolan-2-yl]-5-methyl-6-phenylsulfanylhex-4-enoxy]-dimethylsilane
• CAS: 121400-93-9
• 化学式: C₃₄H₅₈O₄SSi
• 分子量: 590.984
• InChiKey: APFHKVPVHUYHKP-ZDCMBMLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.96
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (2R,5R)-2-<(E)-(S)-1-<(tert-butyldimethylsilyl)oxy>-5-methyl-6-(phenylthio)hex-4-enyl>tetrahydro-5-<(S)-1-(methoxymethoxy)-1,5-dimethylhex-4-enyl>-2-methylfuran 在 bis(acetylacetonate)oxovanadium 盐酸 、 叔丁基过氧化氢 、 正丁基锂 、 四甲基乙二胺 、 四丁基氟化铵 、 sodium 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 36.0h， 生成 (2R,5R)-tetrahydro-2-<(2S,5R)-tetrahydro-5-<(1S,4S,5R)-1,4,5-trihydroxy-1,5,9-trimethyldec-8-enyl>furan-2-yl>-5-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-2-methylfuran
  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
• 作为产物：
  描述：

  {(S)-4-Benzyloxy-1-[(2R,5R)-5-((S)-1-methoxymethoxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-butoxy}-tert-butyl-dimethyl-silane 在 四氯化碳 、 氨 、 lithium 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.58h， 生成 (2R,5R)-2-<(E)-(S)-1-<(tert-butyldimethylsilyl)oxy>-5-methyl-6-(phenylthio)hex-4-enyl>tetrahydro-5-<(S)-1-(methoxymethoxy)-1,5-dimethylhex-4-enyl>-2-methylfuran
  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：——
• HASHIMOTO, MASARU;YANAGIYA, MITSUTOSHI;SHIRAHAMA, HARUHISA, CHEM. LETT.,(1988) N 4, 645-646
  作者：HASHIMOTO, MASARU、YANAGIYA, MITSUTOSHI、SHIRAHAMA, HARUHISA

  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.