(2S,3S,4R,5S)-3-(tert-butyldimethylsiloxy)-2,4-dimethyl-1,5-heptanediol | 620592-22-5

• 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: (2S,3S,4R,5S)-3-(tert-butyldimethylsiloxy)-2,4-dimethyl-1,5-heptanediol
• 英文别名: (2S,3S,4R,5S)-3-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethylheptane-1,5-diol
• CAS: 620592-22-5
• 化学式: C₁₅H₃₄O₃Si
• 分子量: 290.519
• InChiKey: ZUPBINNKOUWCPX-CRWXNKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  19
• 可旋转键数：
  8
• 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：

  (2S,3S,4R,5S)-3-(tert-butyldimethylsiloxy)-2,4-dimethyl-1,5-heptanediol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以56%的产率得到(3R,4R,5R,6S)-4-(tert-butyldimethylsiloxy)-6-ethyl-3,5-dimethyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Chemoenzymatic enantioselective synthesis of the polypropionate acid moiety of dolabriferol

  摘要：

  Dolabriferol is a marine polypropionate characterized by an unusual non-contiguous carbon skeleton. The two polypropionate subunits are linked by all ester function. The acid moiety of dolabriferol (ee-97%,) was synthesized in five steps and 58% overall yield via the enzymatic desymmetrization of meso-(anti anti)-2,4-dimethyl-1,3,5-pentanetriol. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00587-1
• 作为产物：
  描述：

  Xylitol, 2,4-dideoxy-3-O-[(1,1-dimethylethyl)dimethylsilyl]-2,4-dimethyl- 在 3 A molecular sieve 、 戴斯-马丁氧化剂 、 磷脂酶B 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2S,3S,4R,5S)-3-(tert-butyldimethylsiloxy)-2,4-dimethyl-1,5-heptanediol
  参考文献：
  名称：

  Chemoenzymatic enantioselective synthesis of the polypropionate acid moiety of dolabriferol

  摘要：

  Dolabriferol is a marine polypropionate characterized by an unusual non-contiguous carbon skeleton. The two polypropionate subunits are linked by all ester function. The acid moiety of dolabriferol (ee-97%,) was synthesized in five steps and 58% overall yield via the enzymatic desymmetrization of meso-(anti anti)-2,4-dimethyl-1,3,5-pentanetriol. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00587-1

文献信息

• Chemoenzymatic enantioselective synthesis of the polypropionate acid moiety of dolabriferol
  作者：Robert Chênevert、Gabriel Courchesne、Dave Caron

  DOI：10.1016/s0957-4166(03)00587-1

  日期：2003.9

  Dolabriferol is a marine polypropionate characterized by an unusual non-contiguous carbon skeleton. The two polypropionate subunits are linked by all ester function. The acid moiety of dolabriferol (ee-97%,) was synthesized in five steps and 58% overall yield via the enzymatic desymmetrization of meso-(anti anti)-2,4-dimethyl-1,3,5-pentanetriol. (C) 2003 Elsevier Ltd. All rights reserved.