(+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene | 291751-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene
• 英文别名: [(1R,2R,3R,4S,5S)-2-[(4-methoxyphenyl)methoxy]-4-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-yl]oxy-tri(propan-2-yl)silane
• CAS: 291751-48-9
• 化学式: C₂₅H₄₀O₄Si
• 分子量: 432.676
• InChiKey: QQGBEQVZKRTYDL-GFKHSOBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene 在 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到(+)-(2R,3S,4S,5R,6S)-[2-(hydroxymethyl)-3-p-(methoxybenzyloxy)-5-methyl-4-(triisopropylsilyloxy)tetrahydropyran-6-yl]methanol
  参考文献：
  名称：

  Synthesis of the C38−C44 Segment of Altohyrtin A − With an Addendum on the Preparation of 8-Oxabicyclo[3.2.1]oct-6-en-3-one

  摘要：

  The densely funkctionalized C38-C44 segment F of altohyrtin A with its five contiguous stereogenic centers was prepared in 10 steps and in 28 % overall yield (two steps per stereogenic center), from 8-oxabicyclo[3.2.1]oct-6-en-3-one as a template. The preparation of the title compound 1, m.p. 38 degrees C, is described on a 0.5-m scale in a three-step-two-stage reaction from acetone and furan. The oxacycle was stored without change at room temperature.

  DOI：

  10.1002/1099-0690(200006)2000:12<2195::aid-ejoc2195>3.0.co;2-c
• 作为产物：
  描述：

  (1R,5R)-3-triethylsilanyloxy-8-oxabicyclo[3.2.1]oct-2,6-diene 在 咪唑 、 2,6-二甲基吡啶 、 盐酸 、 四甲基乙二胺 、 L-Selectride 、 sodium hydride 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.83h， 生成 (+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene
  参考文献：
  名称：

  Synthesis of the C38−C44 Segment of Altohyrtin A − With an Addendum on the Preparation of 8-Oxabicyclo[3.2.1]oct-6-en-3-one

  摘要：

  The densely funkctionalized C38-C44 segment F of altohyrtin A with its five contiguous stereogenic centers was prepared in 10 steps and in 28 % overall yield (two steps per stereogenic center), from 8-oxabicyclo[3.2.1]oct-6-en-3-one as a template. The preparation of the title compound 1, m.p. 38 degrees C, is described on a 0.5-m scale in a three-step-two-stage reaction from acetone and furan. The oxacycle was stored without change at room temperature.

  DOI：

  10.1002/1099-0690(200006)2000:12<2195::aid-ejoc2195>3.0.co;2-c

文献信息

• Synthesis of the C38−C44 Segment of Altohyrtin A − With an Addendum on the Preparation of 8-Oxabicyclo[3.2.1]oct-6-en-3-one
  作者：H. Kim、H. Martin R. Hoffmann

  DOI：10.1002/1099-0690(200006)2000:12<2195::aid-ejoc2195>3.0.co;2-c

  日期：2000.6

  The densely funkctionalized C38-C44 segment F of altohyrtin A with its five contiguous stereogenic centers was prepared in 10 steps and in 28 % overall yield (two steps per stereogenic center), from 8-oxabicyclo[3.2.1]oct-6-en-3-one as a template. The preparation of the title compound 1, m.p. 38 degrees C, is described on a 0.5-m scale in a three-step-two-stage reaction from acetone and furan. The oxacycle was stored without change at room temperature.