(2R*,3S*)-4-(t-butyldimethylsilanyloxy)-2-vinyl-butane-1,3-diol

• 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*,3S*)-4-(t-butyldimethylsilanyloxy)-2-vinyl-butane-1,3-diol
• 英文别名: (2S,3R)-4-[tert-butyl(dimethyl)silyl]oxy-2-ethenylbutane-1,3-diol
• 化学式: C₁₂H₂₆O₃Si
• 分子量: 246.422
• InChiKey: GWENQBCIAIFWPR-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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*,3S*)-4-(t-butyldimethylsilanyloxy)-2-vinyl-butane-1,3-diol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 acrylic acid (1S*,2R*)-1-(t-butyldimethylsilanyloxymethyl)-2-(2,2-dimethylpropanoyloxymethyl)-but-3-enyl ester
  参考文献：
  名称：

  Di- and tetrahydropyrans with orthogonally protected hydroxymethyl side chains: a synthetic route and the structure elucidation of an unexpected acetal cleavage product

  摘要：

  A synthesis of dihydropyrans with orthogonally protected hydroxymethyl side chains is presented in this contribution. Key steps of the synthesis are the regioselective epoxide opening using vinyl cuprate reagents, selective protection of primary alcohols and ring closing metathesis. A strategy based on the intermediate formation of a rigid bicyclic acetal turned out to be unsuccessful due to the unexpected formation of an annellated furanopyran rearrangement product 6. Elucidation of the structure was achieved using one- and two-dimensional NMR-methods. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00913-4
• 作为产物：
  描述：

  (Z)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol 在 叔丁基过氧化氢 、 copper(l) iodide 、 bis(acetylacetonate)oxovanadium 作用下， 以 四氢呋喃 、 乙醚 、 癸烷 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (2R*,3S*)-4-(t-butyldimethylsilanyloxy)-2-vinyl-butane-1,3-diol
  参考文献：
  名称：

  Di- and tetrahydropyrans with orthogonally protected hydroxymethyl side chains: a synthetic route and the structure elucidation of an unexpected acetal cleavage product

  摘要：

  A synthesis of dihydropyrans with orthogonally protected hydroxymethyl side chains is presented in this contribution. Key steps of the synthesis are the regioselective epoxide opening using vinyl cuprate reagents, selective protection of primary alcohols and ring closing metathesis. A strategy based on the intermediate formation of a rigid bicyclic acetal turned out to be unsuccessful due to the unexpected formation of an annellated furanopyran rearrangement product 6. Elucidation of the structure was achieved using one- and two-dimensional NMR-methods. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00913-4