[(2R,3S,6R)-6-Allyl-3-(4-methoxy-phenoxy)-3,6-dihydro-2H-pyran-2-ylmethoxy]-tert-butyl-dimethyl-silane | 859215-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(2R,3S,6R)-6-Allyl-3-(4-methoxy-phenoxy)-3,6-dihydro-2H-pyran-2-ylmethoxy]-tert-butyl-dimethyl-silane
• 英文别名: tert-butyl-[[(2R,3S,6R)-3-(4-methoxyphenoxy)-6-prop-2-enyl-3,6-dihydro-2H-pyran-2-yl]methoxy]-dimethylsilane
• CAS: 859215-06-8
• 化学式: C₂₂H₃₄O₄Si
• 分子量: 390.595
• InChiKey: PBYNKISBGLKYPY-HLAWJBBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  [(2R,3S,6R)-6-Allyl-3-(4-methoxy-phenoxy)-3,6-dihydro-2H-pyran-2-ylmethoxy]-tert-butyl-dimethyl-silane 在 四氧化锇 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 偶氮二甲酸二异丙酯 、 PS-diethylenetriamine 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 11.46h， 生成 [(2R,3S,6R)-6-(2-aminooxyethyl)-3-(4-methoxyphenoxy)-3,6-dihydro-2H-pyran-2-yl]methyl N-propylcarbamate
  参考文献：
  名称：

  Convergent Synthesis of a Complex Oxime Library Using Chemical Domain Shuffling

  摘要：

  yThe synthesis of a complex hybrid oxime library is reported utilizing convergent ligation of alkoxyamine and carbonyl monomers via "chemical domain shuffling". Initial biological screening of the library against human small cell lung carcinoma (A549) cells led to the identification of a novel hybrid dimer in contrast to the corresponding monomeric compounds which were found to be inactive.

  DOI：

  10.1021/ol051023r
• 作为产物：
  描述：

  (2R,3S,6R)-1-tert-butyldimethylsilyloxy-3-hydroxy-2,6-epoxynona-4,8-diene 在 (S,S)-DACH-phenyl Trost ligand 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.84h， 生成 [(2R,3S,6R)-6-Allyl-3-(4-methoxy-phenoxy)-3,6-dihydro-2H-pyran-2-ylmethoxy]-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Convergent Synthesis of a Complex Oxime Library Using Chemical Domain Shuffling

  摘要：

  yThe synthesis of a complex hybrid oxime library is reported utilizing convergent ligation of alkoxyamine and carbonyl monomers via "chemical domain shuffling". Initial biological screening of the library against human small cell lung carcinoma (A549) cells led to the identification of a novel hybrid dimer in contrast to the corresponding monomeric compounds which were found to be inactive.

  DOI：

  10.1021/ol051023r

文献信息

• Exploring Skeletal Diversity via Ring Contraction of Glycal-Derived Scaffolds
  作者：Adam R. Yeager、Geanna K. Min、John A. Porco,、Scott E. Schaus

  DOI：10.1021/ol0618252

  日期：2006.10.1

  Aryl ether C-glycoside scaffolds have been prepared from tri-O-acetyl-D-glucal by C-glycosylation followed by allylic substitution with phenols mediated by Pd(0). The aryl ethers were subjected to either [3,3]-sigmatropic rearrangement to produce 3-pyranyl-phenols or Au(III)-mediated ring contraction to create highly substituted tetrahydrofurans. [structure: see text]

  芳基醚C-糖苷支架已由C-糖基化，然后由Pd（0）介导的苯酚进行烯丙基取代，由三-O-乙酰基-D-葡糖醛制备。使芳基醚经历[3,3]-σ重排以产生3-吡喃基-酚或Au（III）介导的环收缩以产生高度取代的四氢呋喃。[结构：见文字]