(1R,2R)-1-Phenyl-3-(phenylthio)propane-1,2-diol | 155930-92-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1R,2R)-1-Phenyl-3-(phenylthio)propane-1,2-diol
• 英文别名: (1R,2R)-1-phenyl-3-phenylsulfanylpropane-1,2-diol
• CAS: 155930-92-0
• 化学式: C₁₅H₁₆O₂S
• 分子量: 260.357
• InChiKey: VCJCTTNJBUCKDX-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲氧基丙烯 、 (1R,2R)-1-Phenyl-3-(phenylthio)propane-1,2-diol 在 氢气 作用下， 以100%的产率得到(4R,5R)-2,2-Dimethyl-4-phenyl-5-phenylsulfanylmethyl-[1,3]dioxolane
  参考文献：
  名称：

  Enantioselective synthesis of goniobutenolides A and B

  摘要：

  Goniobutenolides A and B were synthesized in the enantiopure Forms, employing the asymmetric dihydroxylation and cyclic sulfate rearrangement-opening reactions as the key stereocenter-forming steps.

  DOI：

  10.1016/0040-4039(95)00166-a
• 作为产物：
  描述：

  1-(tert-butyldimethylsilyloxy)-3-phenyl-2-propene 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 甲基磺酰胺 、 AD-mix-β 、 硫酸 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 11.67h， 生成 (1R,2R)-1-Phenyl-3-(phenylthio)propane-1,2-diol
  参考文献：
  名称：

  An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction

  摘要：

  A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction. Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate. Upon desilylation, this compound undergoes a Payne-type rearrangement. Nucleophilic epoxide-opening then provides an erythro-2,3-diol. The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel. Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures. Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, N--(3), (OAc)-O--, (CN)-C--, halides as well as carbon nucleophiles and hydride.

  DOI：

  10.1021/jo00088a045

文献信息

• Ko Soo Y., Malik Majbeen, Dickinson A. Frances, J. Org. Chem, 59 (1994) N 9, S 2570-2576
  作者：Ko Soo Y., Malik Majbeen, Dickinson A. Frances

  DOI：——

  日期：——
• An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction
  作者：Soo Y. Ko、Majbeen Malik、A. Frances Dickinson

  DOI：10.1021/jo00088a045

  日期：1994.5

  A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction. Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate. Upon desilylation, this compound undergoes a Payne-type rearrangement. Nucleophilic epoxide-opening then provides an erythro-2,3-diol. The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel. Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures. Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, N--(3), (OAc)-O--, (CN)-C--, halides as well as carbon nucleophiles and hydride.
• Enantioselective synthesis of goniobutenolides A and B
  作者：Soo Y. Ko、Joanne Lerpiniere

  DOI：10.1016/0040-4039(95)00166-a

  日期：1995.3

  Goniobutenolides A and B were synthesized in the enantiopure Forms, employing the asymmetric dihydroxylation and cyclic sulfate rearrangement-opening reactions as the key stereocenter-forming steps.