(2R,3S,4R)-5-<(tert-Butyldimethylsilyl)oxy>-1,2-O-isopropylidenepentane-1,2,3,4-tetrol | 155930-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-5-<(tert-Butyldimethylsilyl)oxy>-1,2-O-isopropylidenepentane-1,2,3,4-tetrol
• 英文别名: (1S,2R)-3-[tert-butyl(dimethyl)silyl]oxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propane-1,2-diol
• CAS: 155930-87-3
• 化学式: C₁₄H₃₀O₅Si
• 分子量: 306.475
• InChiKey: KKINJNPWNHLRLD-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-5-<(tert-Butyldimethylsilyl)oxy>-1,2-O-isopropylidenepentane-1,2,3,4-tetrol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 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 为溶剂， 反应 5.67h， 生成 (2R,3S,4R)-5-(Phenylthio)-1,2-O-isopropylidenepentane-1,2,3,4-tetrol
  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
• 作为产物：
  描述：

  (S)-4,5-异亚丙基-2-戊醇 在 4-二甲氨基吡啶 、 甲基磺酰胺 、 AD-mix-β 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (2R,3S,4R)-5-<(tert-Butyldimethylsilyl)oxy>-1,2-O-isopropylidenepentane-1,2,3,4-tetrol
  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

• 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.