(4S,5S)-4,5-diphenyl-1,3,2-dioxathiolane 2-oxide | 204778-93-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4S,5S)-4,5-diphenyl-1,3,2-dioxathiolane 2-oxide
• CAS: 204778-93-8
• 化学式: C₁₄H₁₂O₃S
• 分子量: 260.313
• InChiKey: QFXSAPIDISAYKZ-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4,5-diphenyl-1,3,2-dioxathiolane 2-oxide 在 sodium azide 、 palladium on carbon 、 氢气 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 tert-Butyl ((1R,2S)-2-hydroxy-1,2-diphenylethyl)carbamate
  参考文献：
  名称：

  Enantioselective synthesis of (1S,2R)-ephenamine

  摘要：

  DOI：

  10.1016/j.tetasy.2016.02.013
• 作为产物：
  描述：

  (S,S)-(-)-氢化苯偶姻 在 氯化亚砜 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 生成 (4S,5S)-4,5-diphenyl-1,3,2-dioxathiolane 2-oxide
  参考文献：
  名称：

  Conformational Preferences of RNase A C-Peptide Derivatives Containing a Highly Constrained Analogue of Phenylalanine

  摘要：

  Both enantiomers of a highly constrained derivative of phenylalanine, FiFi, were prepared in optically pure form. Studies were performed to elucidate the effects of substituting this amino acid for phenylalanine in RN-24, a derivative of the RNase A C-peptide. Thus RN-24, and the analogues 9 and 10, in which Phe-8 was replaced by each of the enantiomers of FiFi, were prepared. Comparative circular dichroism (CD) experiments indicated relative tendencies to adopt helical structures, and variable-temperature CD studies showed the relative ease with which these conformations were lost at elevated temperatures. These observations were rationalized via computer-assisted molecular modeling, which showed that the phenyl groups of (R,R)-FiFi in the peptidomimetic 9 can be accommodated via distortion of the helical conformations and that such distorted conformations persist as the temperature is increased. Conversely, intolerable contacts occur in an analogous conformation of the (S,S)-FiFi peptidomimetic 10 and these preclude helicity. Consistent with these observations, molecular dynamics studies of these peptidomimetics at 276 K indicate that helical conformations of 9 and RN-24 are observable under conditions in which the analogous conformation of 10 is lost. Overall, these studies demonstrate that cyclopropane amino acids can be used to enforce elements of secondary structure (albeit distorted) or to preclude them altogether.

  DOI：

  10.1021/ja981153d

文献信息

• Reaction of 1,2-Cyclic Sulfites with Some Soft Nucleophiles. Formation of Enantiomerically Pure gamma-Lactones.
  作者：Kirsten Nymann、John S. Svendsen、Eli Ranes、Jaroslav Riha、Eugen Mesaros、Alin Mihis、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0338

  日期：——

  The reaction between 1,2-cyclic sulfites and soft carbon centered nucleophiles has been investigated. For monosubstituted cyclic sulfites, the main products were gamma-lactones or acetoxy esters. For 1,2-disubstituted cyclic sulfites. cyclopropanes. carbonate and dioxolanes were the main products, A mechanistic rationale for the product formation is presented.
• Conformational Preferences of RNase A <i>C</i>-Peptide Derivatives Containing a Highly Constrained Analogue of Phenylalanine
  作者：Destardi Moye-Sherman、Song Jin、Inhye Ham、Dongyeol Lim、J. Martin Scholtz、Kevin Burgess

  DOI：10.1021/ja981153d

  日期：1998.9.1

  Both enantiomers of a highly constrained derivative of phenylalanine, FiFi, were prepared in optically pure form. Studies were performed to elucidate the effects of substituting this amino acid for phenylalanine in RN-24, a derivative of the RNase A C-peptide. Thus RN-24, and the analogues 9 and 10, in which Phe-8 was replaced by each of the enantiomers of FiFi, were prepared. Comparative circular dichroism (CD) experiments indicated relative tendencies to adopt helical structures, and variable-temperature CD studies showed the relative ease with which these conformations were lost at elevated temperatures. These observations were rationalized via computer-assisted molecular modeling, which showed that the phenyl groups of (R,R)-FiFi in the peptidomimetic 9 can be accommodated via distortion of the helical conformations and that such distorted conformations persist as the temperature is increased. Conversely, intolerable contacts occur in an analogous conformation of the (S,S)-FiFi peptidomimetic 10 and these preclude helicity. Consistent with these observations, molecular dynamics studies of these peptidomimetics at 276 K indicate that helical conformations of 9 and RN-24 are observable under conditions in which the analogous conformation of 10 is lost. Overall, these studies demonstrate that cyclopropane amino acids can be used to enforce elements of secondary structure (albeit distorted) or to preclude them altogether.
• Enantioselective synthesis of (1S,2R)-ephenamine
  作者：Ramandeep Kaur、Satyendra Kumar Pandey

  DOI：10.1016/j.tetasy.2016.02.013

  日期：2016.5