(2S,3R)-1,2-epoxy-3-(methoxymethoxy)-3,7-dimethyl-6-octene | 121400-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S,3R)-1,2-epoxy-3-(methoxymethoxy)-3,7-dimethyl-6-octene
• 英文别名: (2S)-2-[(2R)-2-(methoxymethoxy)-6-methylhept-5-en-2-yl]oxirane
• CAS: 121400-91-7
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: DOWFTZLWOFJRCK-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1,2-epoxy-3-(methoxymethoxy)-3,7-dimethyl-6-octene 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：

  Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester 在 4-二甲氨基吡啶 、 potassium carbonate 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 60.67h， 生成 (2S,3R)-1,2-epoxy-3-(methoxymethoxy)-3,7-dimethyl-6-octene
  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

• 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
• 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：——
• HASHIMOTO, MASARU;HARIGAYA, HIROKO;YANAGIYA, MITSUTOSHI;SHIRAHAMA, HARUHI+, TETRAHEDRON LETT., 29,(1988) N 46, C. 5947-5948
  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.