(3S,6S)-6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-ol | 329684-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (3S,6S)-6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-ol
• 英文别名: (3R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-3,6-dihydro-2H-pyran-3-ol
• CAS: 329684-93-7
• 化学式: C₁₁H₂₂O₃Si
• 分子量: 230.379
• InChiKey: XXLQTOLVNZXFAX-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,6S)-6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-ol 在 甲醇 、 三氟化硼乙醚 、 potassium carbonate 、 三乙胺 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (2R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-2H-pyran-5-one
  参考文献：
  名称：

  立体选择性亲核取代的6-（叔丁基二甲基甲硅烷氧基）-3,6-二氢-2 H-吡喃-3-基乙酸酯：在合成NK 1受体拮抗剂中的应用

  摘要：

  手性的反应顺式-和反式-6-（叔-butyldimethylsilyloxy）-3,6-二氢-2 H ^ -吡喃-3-基乙酸酯在存在各种亲核（烯丙基三甲基硅烷，bistrimethylsilylacetylene，苄醇，苄基氨基甲酸叔丁酯等）路易斯酸的生成，以反式选择性好至极好产率得到相应的2，3-不饱和吡喃衍生物。还描述了在NK 1拮抗剂的合成中的应用。

  DOI：

  10.1016/j.tetlet.2007.03.104
• 作为产物：
  描述：

  2,6-二氢-6-羟基-3(3H)-吡喃酮 在 2,6-二甲基吡啶 、 甲醇 、 sodium tetrahydroborate 、 cerium(III) chloride 、 lipase AK 、 4 A molecular sieve 作用下， 以 phosphate buffer 、 二氯甲烷 、 丙酮 为溶剂， 反应 116.0h， 生成 (3S,6S)-6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  Efficient and practical synthesis of both enantiomers of 6-silyloxy-3-pyranone derivatives

  摘要：

  Lipase catalyzed kinetic resolution of racemic cis-6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-ol (rac)-1 was achieved in high enantiomeric excess. Transesterification of (rac)-1 with vinylacetate in 'BuOMe yielded the alcohol (3S,6R)-1 in 99.0% ee, whereas (3R,6S)-1 was obtained, in 99.0% ee, by the lipase catalyzed ester hydrolysis of acetate (3R,6S)-2, which was obtained along with the transesterification. Both (3S,6R)-1 and (3R,6S)-1 were subjected to oxidation to provide the corresponding 6-silyloxy-3-pyranone (6R)-3 and (6S)-3, respectively. Application to the synthesis of 7, which is the key intermediate of asymmetric synthesis of pseudomonic acid A 9 is also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00424-9

文献信息

• Stereoselective nucleophilic substitution of 6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-yl acetate: application to the synthesis of a NK1 receptor antagonist
  作者：Kazutoshi Sugawara、Tomiki Hashiyama

  DOI：10.1016/j.tetlet.2007.03.104

  日期：2007.5

  Reaction of chiral cis- and trans-6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-yl acetates with various nucleophiles (allyltrimethylsilane, bistrimethylsilylacetylene, benzyl alcohol, benzyl carbamate etc.) in the presence of a Lewis acid gave the corresponding 2,3-unsaturated pyran derivatives in good to excellent yield with trans selectivity. Application to the synthesis of NK1 antagonist

  手性的反应顺式-和反式-6-（叔-butyldimethylsilyloxy）-3,6-二氢-2 H ^ -吡喃-3-基乙酸酯在存在各种亲核（烯丙基三甲基硅烷，bistrimethylsilylacetylene，苄醇，苄基氨基甲酸叔丁酯等）路易斯酸的生成，以反式选择性好至极好产率得到相应的2，3-不饱和吡喃衍生物。还描述了在NK 1拮抗剂的合成中的应用。
• Efficient and practical synthesis of both enantiomers of 6-silyloxy-3-pyranone derivatives
  作者：Kazutoshi Sugawara、Yasuhiro Imanishi、Tomiki Hashiyama

  DOI：10.1016/s0957-4166(00)00424-9

  日期：2000.11

  Lipase catalyzed kinetic resolution of racemic cis-6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-ol (rac)-1 was achieved in high enantiomeric excess. Transesterification of (rac)-1 with vinylacetate in 'BuOMe yielded the alcohol (3S,6R)-1 in 99.0% ee, whereas (3R,6S)-1 was obtained, in 99.0% ee, by the lipase catalyzed ester hydrolysis of acetate (3R,6S)-2, which was obtained along with the transesterification. Both (3S,6R)-1 and (3R,6S)-1 were subjected to oxidation to provide the corresponding 6-silyloxy-3-pyranone (6R)-3 and (6S)-3, respectively. Application to the synthesis of 7, which is the key intermediate of asymmetric synthesis of pseudomonic acid A 9 is also described. (C) 2000 Elsevier Science Ltd. All rights reserved.