(S)-2-t-butyldimethylsilyloxymethylglycidol | 173215-95-7

• 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)-2-t-butyldimethylsilyloxymethylglycidol
• CAS: 173215-95-7
• 化学式: C₁₀H₂₂O₃Si
• 分子量: 218.368
• InChiKey: IYWLOJWRYYTWLN-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2H-吡喃 、 (S)-2-t-butyldimethylsilyloxymethylglycidol 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到tert-butyl-dimethyl-[[(2R)-2-(oxan-2-yloxymethyl)oxiran-2-yl]methoxy]silane
  参考文献：
  名称：

  Enantioselective Synthesis of a 3,5,5-Trialkylated Tetronic Acid Derivative

  摘要：

  A convenient and enantioselective method for the synthesis of 3,5,5-trialkylated tetronic acid has been developed. The Dieckmann-type condensation of enantioenriched alpha-acyloxy-alpha,alpha-dialkylated acetic acid ester (11) proceeded in the presence of lithium hexamethyldisilazide, providing the expected tetronic acid derivative (12) after quenching with methoxymethyl chloride. The product (12) was converted into a doubly prenylated tetronic acid derivative (13), which constitutes a substructure of perforatumone, a newly isolated polycyclic polyprenylated acylphloroglucinol-type natural product.

  DOI：

  10.3987/com-08-s(f)11
• 作为产物：
  描述：

  2-(tert-butyl-dimethyl-silanyloxymethyl)-prop-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(S)-2-t-butyldimethylsilyloxymethylglycidol
  参考文献：
  名称：

  Enantioselective Synthesis of a 3,5,5-Trialkylated Tetronic Acid Derivative

  摘要：

  A convenient and enantioselective method for the synthesis of 3,5,5-trialkylated tetronic acid has been developed. The Dieckmann-type condensation of enantioenriched alpha-acyloxy-alpha,alpha-dialkylated acetic acid ester (11) proceeded in the presence of lithium hexamethyldisilazide, providing the expected tetronic acid derivative (12) after quenching with methoxymethyl chloride. The product (12) was converted into a doubly prenylated tetronic acid derivative (13), which constitutes a substructure of perforatumone, a newly isolated polycyclic polyprenylated acylphloroglucinol-type natural product.

  DOI：

  10.3987/com-08-s(f)11

文献信息

• Enzymatic preparation of optically active 2-acetoxymethylglycidol, a new chiral building block in natural product synthesis.
  作者：Young-Bae Seu、Yung-Hee Kho

  DOI：10.1016/s0040-4039(00)60920-6

  日期：1992.11

  Asymmetric hydrolysis of geminally disubstituted achiral diacetate 2 with lipase PPL yielded optically active (R)-(−)-2-acetoxymethylglycidol 3 and its reduction gave compound 6, useful as the tert-alcohol chiral building block.

  用脂肪酶PPL对二元双取代的非手性二乙酸酯2的不对称水解产生旋光的（R）-（-）-2-乙酰氧基甲基缩水甘油3，并将其还原，得到化合物6，可用作叔醇手性结构单元。
• Preparation of enantiomerically pure (R)-2-butyryloxymethylglycidol by lipase-catalyzed asymmetric hydrolysis
  作者：Young-Bae Seu、Taeg-Kyeong Lim、Chang-Jin Kim、Sun-Chul Kang

  DOI：10.1016/0957-4166(95)00397-5

  日期：1995.12

  Optically active epoxy alcohol, (R)-2-butyryloxymethylglycidol 3 which is the precursor of a tert-alcohol chiral building block was obtained in high enantiomeric purity, 98.7% e.e., by lipase-catalyzed asymmetric hydrolysis using a phosphate buffer and organic co-solvent system in 95% of chemical yield.