Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate | 162264-90-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate
• 英文别名: methyl 2-(2R,3R,4S)-5-oxo-4-(phenylthio)-2-(2-tert-butyldiphenylsilyloxy)ethyl-tetrahydrofuran-3-yl-acetate；methyl 2-[(2R,3R,4S)-2-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-5-oxo-4-phenylsulfanyloxolan-3-yl]acetate
• CAS: 162264-90-6
• 化学式: C₃₁H₃₆O₅SSi
• 分子量: 548.775
• InChiKey: XWOLFTQDSINJLU-QQJNOOCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate 在 sodium hydroxide 、 pyridine-SO3 complex 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one
  参考文献：
  名称：

  γ-Lactones as templates in ring-closing metathesis: Enantioselective synthesis of medium sized carbocycles fused to butyrolactones

  摘要：

  DOI：

  10.1016/j.jorganchem.2006.08.021
• 作为产物：
  描述：

  methyl (4R)-4-[(phenylthio)-acetoxy]-6-tert-butyldiphenylsilyloxy-hexen-2(E)-oate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以95%的产率得到Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate
  参考文献：
  名称：

  γ-Lactones as templates in ring-closing metathesis: Enantioselective synthesis of medium sized carbocycles fused to butyrolactones

  摘要：

  DOI：

  10.1016/j.jorganchem.2006.08.021

文献信息

• Stereoselective Synthesis of Highly Substituted .gamma.-Lactones and Butenolides by Intramolecular Michael Addition of Enantiomerically Enriched .gamma.-[(Phenylthio)acyl]oxy .alpha.,.beta.-Unsaturated Esters
  作者：Carmen M. Rodriguez、Tomas Martin、Miguel A. Ramirez、Victor S. Martin

  DOI：10.1021/jo00095a022

  日期：1994.8

  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.
• An approach to the stereocontrolled synthesis of polysubstituted chiral butenolides and γ-lactones
  作者：Carmen Ma Rodríguez、Victor S. Martín

  DOI：10.1016/s0040-4039(00)71265-2

  日期：1991.5

  The enantioselective synthesis of polysubstituted butenolides and gamma-lactones by an intramolecular Michael addition of chiral thiophenylacetates of gamma-hydroxy-alpha,beta-unsaturated esters is described.
• γ-Lactones α,β- and β,γ-fused to carbocycles as novel antiproliferative drugs
  作者：Leticia G. León、Rubén P. Machín、Carmen M. Rodríguez、José L. Ravelo、Víctor S. Martín、José M. Padrón

  DOI：10.1016/j.bmcl.2008.08.098

  日期：2008.10

  A set of gamma-lactones alpha,beta-fused and beta,gamma-fused to carbocycles have been synthesized and evaluated for their in vitro antiproliferative activities using the human cancer cell lines SW1573 (lung), T-47D (breast) and WiDr (colon). The compounds are obtained by intramolecular ring closing metathesis of the corresponding dienes. Active compounds exhibited GI(50) values in the range 8-18 mu M. A structure-activity relationship is also discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• 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：——
• γ-Lactones as templates in ring-closing metathesis: Enantioselective synthesis of medium sized carbocycles fused to butyrolactones
  作者：José Luis Ravelo、Carmen Ma Rodríguez、Víctor S. Martín

  DOI：10.1016/j.jorganchem.2006.08.021

  日期：2006.12