Methyl (2R,3R,4R)-<4-methyl-5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate | 141811-48-5

• 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: Methyl (2R,3R,4R)-<4-methyl-5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate
• 英文别名: (2R,3R,4R)-2-methyl-2-phenylthio-3-methoxycarbonylmethyl-4-(2'-tert-butyldiphenylsilyloxy)ethyl-γ-butyrolactone；methyl 2-[(2R,3R,4R)-2-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-4-methyl-5-oxo-4-phenylsulfanyloxolan-3-yl]acetate
• CAS: 141811-48-5
• 化学式: C₃₂H₃₈O₅SSi
• 分子量: 562.802
• InChiKey: KFKXNOUATAZFNV-DMBDEWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl (2R,3R,4R)-<4-methyl-5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate 在 ruthenium trichloride 过碘酸 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以91%的产率得到(2R,3R,4R)-2-methyl-2-benzenesulphonyl-3-methoxycarbonylmethyl-4-(2'-tert-butyldiphenylsilyloxy)ethyl-γ-butyrolactone
  参考文献：
  名称：

  使用催化四氧化钌将硫化物简单有效地氧化为砜

  摘要：

  报道了在四相体系（CCl 4，CH 3 CN，H 2 O）中，使用四氧化钌作为催化剂，高碘酸作为化学计量的氧化剂将硫化物氧化为砜的方法。

  DOI：

  10.1016/s0040-4020(01)88494-5
• 作为产物：
  描述：

  (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-(2-phenylsulfanyl-propionyloxy)-hex-2-enoic acid methyl ester 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 4.0h， 以95%的产率得到Methyl (2R,3R,4R)-<4-methyl-5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted .gamma.-Lactones and Butenolides by Intramolecular Michael Addition of Enantiomerically Enriched .gamma.-[(Phenylthio)acyl]oxy .alpha.,.beta.-Unsaturated Esters

  摘要：

  The synthesis of polysubstituted gamma-lactones by the base-induced cyclization of enantiomerically enriched gamma-((phenylthio)acyl)oxy alpha,beta-unsaturated esters obtained from 2,3-epoxy alcohols is described. The procedure is highly stereoselective and compatible with a wide range of functionalities (ester, tetrahydropyranyl ether, silyl ether, etc.). Varying degrees of substitution, including quaternary centers, in the final gamma-lactone were synthesized with excellent stereoselectivity. Useful functional interconversions were successfully demonstrated, in particular those resulting in butenolides. By the use of AM1 it was concluded that the intramolecular Michael reaction can be described as a kinetically controlled reaction in which the relative stability of the transition states for all possible final configurations led to geometries in agreement with the experimental results.

  DOI：

  10.1021/jo00095a022

文献信息

• Rodriguez Carmen M., Martin Tomas, Ramirez Miguel A., Martin iVictor S., J. Org. Chem, 59 (1994) N 16, S 4461-4472
  作者：Rodriguez Carmen M., Martin Tomas, Ramirez Miguel A., Martin iVictor S.

  DOI：——

  日期：——