(3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylsulfanyloxolan-2-one | 129778-50-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylsulfanyloxolan-2-one
• CAS: 129778-50-3
• 化学式: C₂₇H₃₀O₃SSi
• 分子量: 462.685
• InChiKey: HJJSFJSRHLYNSS-SQJMNOBHSA-N

物化性质

• 沸点：
  567.7±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylsulfanyloxolan-2-one 在 四氯化锡 4-二甲氨基吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>thymine
  参考文献：
  名称：

  Stereoselectivity in the Coupling Reaction between 2-Phenylthio-2,3-dideoxyribose and Silylated Pyrimidine Bases

  摘要：

  在SnCl4存在下，2-α-苯硫基-2,3-双脱氧核糖与硅化嘧啶碱基的耦合反应以立体选择性方式进行，得到β-异构体。这些核苷随后通过氧化后进行热消除，转化为2′,3′-双脱氧-2′,3′-双脱氢核苷。

  DOI：

  10.1246/cl.1990.1459
• 作为产物：
  描述：

  5-(羟基甲基)二氢-2(3H)-呋喃酮 在 三氟甲磺酸三甲基硅酯 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylsulfanyloxolan-2-one
  参考文献：
  名称：

  Diastereoselective sulfenylation reactions employing N-phenylthio lactams under nonbasic conditions

  摘要：

  Silyl enol ethers and silyl ketene acetals react with sulfenamides in the presence of trimethylsilyl triflate to give the corresponding trans-sulfenylated ketones and lactones.

  DOI：

  10.1021/jo00033a004

文献信息

• A general method for controlling glycosylation stereochemistry in the synthesis of 2′-deoxyribose nucleosides
  作者：Lawrence J. Wilson、Dennis Liotta

  DOI：10.1016/s0040-4039(00)98793-8

  日期：1990.1

  Glycosylation reactions of 2-arylsulfinyl-O-acetylribosides6 with silylated thymine11 produce 2′-deoxyribose nucleosides with high β-selectivity. An application of this directing effect in the synthesis of the antiretroviral agent D4T,2, is described.

  2-芳基亚磺酰基-O-乙酰基核糖苷6与甲硅烷基化的胸腺嘧啶11的糖基化反应产生具有高β-选择性的2'-脱氧核糖核苷。描述了这种指导作用在抗逆转录病毒药D4T，2的合成中的应用。
• Stereoselective Synthesis of Highly Substituted .gamma.-Lactones by Diastereoselective Alkylation of .alpha.-(Benzenesulfonyl) Derivatives with Unusual Facial Selectivity
  作者：Carmen M. Rodriquez、Tomas Martin、Miguel A. Ramirez、Victor S. Martin

  DOI：10.1021/jo00105a027

  日期：1994.12

  The oxidation of alpha-(phenylthio) gamma-lactones obtained by the base-induced cyclization of enantiomerically enriched gamma-[(phenylthio) acyl]-alpha,beta-unsaturated esters to sulfones in those cases where the a-carbon has an available proton and further basic alkylation led to an unexpected facial selectivity. The reaction proceeded smoothly with alkylating agents and unsaturated carbonyl compounds, but was unsuccessful when an addition to carbonyl derivatives was attempted. The alkylation reaction was performed over a wide range of substituted substrates in order to investigate the scope and limitations of the method and to have information about the possible origin of the selectivity. The application of the alkylation reaction was extended to the synthesis of bicyclic systems, including a cyclobutane with total stereochemical control. The presence of the alpha-(benzenesulfonyl) group is shown to be essential to achieve the facial selection. In order to rationalize the stereochemical results, extensive semiempirical calculations were performed. The use of MNDO and AM1 permits rationalization of the fact that the alpha-(benzenesulfonyl) group encumbers a diastereoface of the enolate generated in the ring, leading to the observed stereochemistry.
• KAWAKAMI, HIROSHI;EBATA, TAKASHI;KOSEKI, KOSHI;MATSUSHITA, HAJIME;NAOI, Y+, CHEM. LETT.,(1990) N, C. 1459-1462
  作者：KAWAKAMI, HIROSHI、EBATA, TAKASHI、KOSEKI, KOSHI、MATSUSHITA, HAJIME、NAOI, Y+

  DOI：——

  日期：——