(E)-1-{(2R,5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-pent-3-en-2-one | 756834-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (E)-1-{(2R,5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-pent-3-en-2-one
• 英文别名: (E)-1-[(2R,5S,6S)-6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-5-methyloxan-2-yl]pent-3-en-2-one
• CAS: 756834-63-6
• 化学式: C₁₉H₃₆O₃Si
• 分子量: 340.579
• InChiKey: JZNQFJIEEZAWRH-VIDSBYBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-{(2R,5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-pent-3-en-2-one 在 chromium(VI) oxide 、 氢氟酸 、 高碘酸 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 2.17h， 生成 2,5-dioxopyrrolidin-1-yl 2-((2S,3S,6R)-3-methyl-6-((E)-2-oxopent-3-enyl)tetrahydro-2H-pyran-2-yl)acetate
  参考文献：
  名称：

  Synthesis of Bistramide A

  摘要：

  We have developed an efficient and highly stereocontrolled synthesis of bistramide A, a selective activator of protein kinase C isotype delta. Our synthetic strategy featured a novel bidirectional approach for spiroketal construction based on the ring-opening/cross-metathesis sequence employing a highly strained cyclopropenone acetal. The synthesis afforded the final target with the longest linear sequence of 15 steps and provided unambiguous structural determination of bistramide A, including assignment of the previously unknown C(37) stereochemistry.

  DOI：

  10.1021/ja046588h
• 作为产物：
  描述：

  (3S,4S)-6-[(tert-butyldimethylsilyl)oxy]-4-hydroxy-3-methylhex-1-ene 在 palladium on activated charcoal 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 氢气 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 30.17h， 生成 (E)-1-{(2R,5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-pent-3-en-2-one
  参考文献：
  名称：

  Synthesis of Bistramide A

  摘要：

  We have developed an efficient and highly stereocontrolled synthesis of bistramide A, a selective activator of protein kinase C isotype delta. Our synthetic strategy featured a novel bidirectional approach for spiroketal construction based on the ring-opening/cross-metathesis sequence employing a highly strained cyclopropenone acetal. The synthesis afforded the final target with the longest linear sequence of 15 steps and provided unambiguous structural determination of bistramide A, including assignment of the previously unknown C(37) stereochemistry.

  DOI：

  10.1021/ja046588h

文献信息

• Synthesis of Bistramide A
  作者：Alexander V. Statsuk、Dong Liu、Sergey A. Kozmin

  DOI：10.1021/ja046588h

  日期：2004.8.1

  We have developed an efficient and highly stereocontrolled synthesis of bistramide A, a selective activator of protein kinase C isotype delta. Our synthetic strategy featured a novel bidirectional approach for spiroketal construction based on the ring-opening/cross-metathesis sequence employing a highly strained cyclopropenone acetal. The synthesis afforded the final target with the longest linear sequence of 15 steps and provided unambiguous structural determination of bistramide A, including assignment of the previously unknown C(37) stereochemistry.