(5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-one | 756834-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-one
• 英文别名: (5S,6S)-6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-5-methyloxan-2-one
• CAS: 756834-62-5
• 化学式: C₁₄H₂₈O₃Si
• 分子量: 272.46
• InChiKey: LIZGSPDBZZRNEU-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-one 在 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 氢氟酸 、 二异丁基氢化铝 、 高碘酸 、 N,N'-二环己基碳二亚胺 、 zinc(II) chloride 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.34h， 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 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 25.0h， 生成 (5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-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

• Stereoselective Total Synthesis of Bistramide A
  作者：J. S. Yadav、Lakshindra Chetia

  DOI：10.1021/ol702095n

  日期：2007.10.1

  A highly stereoselective and convergent total synthesis of bistramide A is described. The salient feature of this synthesis is the construction of the spiroketal subunit by hydrolysis of dialkylated tosylmethyl isocyanide derivative derived via alkylation of TosMIC with suitably substituted halohydrin derivatives.

  描述了双立体酰胺A的高度立体选择性和收敛的全合成。该合成的显着特征是通过将TosMIC与合适取代的卤代醇衍生物进行烷基化而衍生的二烷基化的甲苯磺酰基甲基异氰化物衍生物的水解来构建螺环亚基。
• Elaboration of the C(3)-C(12) carbon fragment of calcimycin (A-23187). Formal total synthesis of calcimycin
  作者：Paul A. Grieco、Eric Williams、Hideo Tanaka、Sydney Gilman

  DOI：10.1021/jo01305a044

  日期：1980.8
• 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.