(2R,3R)-1-<(tert-Butyldimethylsilyl)oxy>decane-2,3-diol | 155930-89-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R)-1-<(tert-Butyldimethylsilyl)oxy>decane-2,3-diol
• 英文别名: (2R,3R)-1-[(tert-Butyldimethylsilyl)oxy]decane-2,3-diol；(2R,3R)-1-[tert-butyl(dimethyl)silyl]oxydecane-2,3-diol
• CAS: 155930-89-5
• 化学式: C₁₆H₃₆O₃Si
• 分子量: 304.546
• InChiKey: VPNHOYGKUFRAIB-HUUCEWRRSA-N

物化性质

• 沸点：
  376.4±32.0 °C(predicted)
• 密度：
  0.921±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1-<(tert-Butyldimethylsilyl)oxy>decane-2,3-diol 在 盐酸 、 溴 、 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 73.5h， 生成 (2R,3R)-1,2-epoxy-3-decanol
  参考文献：
  名称：

  Straightforward Synthesis of Panaxytriol:  An Active Component of Red Ginseng

  摘要：

  A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a Cadiot-Chodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.

  DOI：

  10.1021/jo0341665
• 作为产物：
  描述：

  反式-2-癸烯醇 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,3R)-1-<(tert-Butyldimethylsilyl)oxy>decane-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

• 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.
• 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：——
• Straightforward Synthesis of Panaxytriol:  An Active Component of Red Ginseng
  作者：Heedong Yun、Samuel J. Danishefsky

  DOI：10.1021/jo0341665

  日期：2003.5.1

  A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a Cadiot-Chodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.