(S)-5-(tert-butyldimethylsilyloxy)-3-methylpentane-1,3-diol | 95496-32-5

• 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: (S)-5-(tert-butyldimethylsilyloxy)-3-methylpentane-1,3-diol
• CAS: 95496-32-5
• 化学式: C₁₂H₂₈O₃Si
• 分子量: 248.438
• InChiKey: CLXRFBKZTHAAKP-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-5-(tert-butyldimethylsilyloxy)-3-methylpentane-1,3-diol 在 2,6-二甲基吡啶 、 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (R)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(triethylsilyloxy)pentanal
  参考文献：
  名称：

  Synthesis and Spectroscopic Analysis of a Stereoisomer Library of the Phytophthora Mating Hormone α1 and Derived Bis-Mosher Esters

  摘要：

  Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone alpha 1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of H-1, C-13, and (for the Mosher esters) F-19 NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H-1 NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed.

  DOI：

  10.1021/ja2082679
• 作为产物：
  描述：

  5-{[(叔丁基二甲基)甲硅烷基]氧基}戊-2-炔酸乙酯 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 L-(+)-酒石酸二异丙酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.08h， 生成 (S)-5-(tert-butyldimethylsilyloxy)-3-methylpentane-1,3-diol
  参考文献：
  名称：

  Synthesis and Spectroscopic Analysis of a Stereoisomer Library of the Phytophthora Mating Hormone α1 and Derived Bis-Mosher Esters

  摘要：

  Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone alpha 1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of H-1, C-13, and (for the Mosher esters) F-19 NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H-1 NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed.

  DOI：

  10.1021/ja2082679

文献信息

• First practical asymmetric synthesis of R-(−)-and s-(+)-mevalonolactones from a single achiral precursor
  作者：Francesco Bonadies、Giovanni Rossi、Carlo Bonini

  DOI：10.1016/s0040-4039(01)91304-8

  日期：1984.1

  A new asymmetric synthesis of R-(−)- and S-(+)- mevalonolactones is described. Starting from a single achiral precursor, the synthesis proceeds by a nine-steps sequence, Sharpless epoxidation of an appropriate allylic alcohol.

  描述了R-（-）-和S-（+）-甲羟戊内酯的新的不对称合成。从一个非手性前体开始，合成过程按九步顺序进行，即适当的烯丙醇的Sharpless环氧化。