(2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol | 151435-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol
• 英文别名: (2R,3R)-1-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxybutane-2,3-diol
• CAS: 151435-00-6
• 化学式: C₁₇H₃₀O₄Si
• 分子量: 326.508
• InChiKey: PRZUFXMXEFCNMZ-HZPDHXFCSA-N

物化性质

• 沸点：
  421.0±45.0 °C(predicted)
• 密度：
  1.036±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 作用下， 生成 (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate
  参考文献：
  名称：

  Synthesis of carbohydrates and related polyhydroxylated compounds employing asymmetric dihydroxylation. 1. An access to erythro-diols

  摘要：

  Asymmetric dihydroxylation provides an easy access to tetrose: threose directly from the (E)-olefin 1, and erythrose via an irreversible Payne-type rearrangement - opening process of the threitol cyclic sulfate 5.

  DOI：

  10.1016/s0040-4039(00)60654-8
• 作为产物：
  描述：

  (E)-4-(benzyloxy)-2-buten-1-ol 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,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-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：——