(4S)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2R,5R)-5-[(2S)-2-(methoxymethoxy)-6-methylhept-5-en-2-yl]-2-methyloxolan-2-yl]butanal | 121400-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2R,5R)-5-[(2S)-2-(methoxymethoxy)-6-methylhept-5-en-2-yl]-2-methyloxolan-2-yl]butanal
• CAS: 121400-98-4
• 化学式: C₂₅H₄₈O₅Si
• 分子量: 456.739
• InChiKey: GBOBFSXKYUQFSP-BPJRBCGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  31.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2R,5R)-5-[(2S)-2-(methoxymethoxy)-6-methylhept-5-en-2-yl]-2-methyloxolan-2-yl]butanal 在 四氯化碳 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 13.08h， 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
• 作为产物：
  描述：

  (1S)-1-[(2R,5R)-5-[(2S)-2-(methoxymethoxy)-6-methylhept-5-en-2-yl]-2-methyloxolan-2-yl]-4-phenylmethoxybutan-1-ol 在 2,6-二甲基吡啶 、 氨 、 lithium 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 (4S)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2R,5R)-5-[(2S)-2-(methoxymethoxy)-6-methylhept-5-en-2-yl]-2-methyloxolan-2-yl]butanal
  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：——