(2S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl benzoate | 222986-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl benzoate
• 英文别名: (-)-6-(tert-butyldimethylsilanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl benzoate；[(2R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxo-2H-pyran-2-yl] benzoate
• CAS: 222986-42-7
• 化学式: C₁₉H₂₆O₅Si
• 分子量: 362.498
• InChiKey: YENGAUCUEQIFFS-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl benzoate 在 4-二甲氨基吡啶 吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-ethoxycarbonyloxy-5,6-dihydro-2H-pyran-2-yl benzoate
  参考文献：
  名称：

  Syntheses of four d- and l-hexoses via diastereoselective and enantioselective dihydroxylation reactions

  摘要：

  An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols call be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-delta-lactones were synthesized in eight steps and similar to 20% overall yield from furfural. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00031-8
• 作为产物：
  描述：

  (R)-2-(2-furyl)-1,2-ethanediol 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 水 为溶剂， 生成 (2S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl benzoate
  参考文献：
  名称：

  5-取代的α，β-不饱和δ-内酯的对映选择性合成：在苯乙烯基内酯的合成中的应用

  摘要：

  通过对乙烯基呋喃进行Sharpless催化不对称二羟基化反应作为关键步骤，已经实现了高度官能化的5个取代的α，β-不饱和δ-内酯的柔性对映选择性合成。所产生的二醇以高对映体过量产生，并且可以通过短的反应序列立体选择性地转化为差异保护的δ-内酯。

  DOI：

  10.1016/s0040-4039(99)02050-x

文献信息

• De Novo Asymmetric Bio- and Chemocatalytic Synthesis of Saccharides − Stereoselective Formal <i>O</i>-Glycoside Bond Formation Using Palladium Catalysis
  作者：Alex C. Comely、Rienk Eelkema、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/ja0347538

  日期：2003.7.1

  approach to the de novo catalytic asymmetric synthesis of saccharides has been developed. Acetoxypyranones obtained enantiopure by enzymatic resolution have been shown to undergo highly stereoselective palladium-catalyzed formal O-glycoside bond formation. The combination of these protocols can be applied to the iterative asymmetric catalytic synthesis of saccharides.

  已经开发了一种新的综合生物和化学催化方法来从头催化不对称合成糖类。通过酶促拆分获得的对映体纯的乙酰氧基吡喃酮已被证明会经历高度立体选择性的钯催化 O-糖苷键的形成。这些协议的组合可以应用于糖的迭代不对称催化合成。
• Enantioselective synthesis of 5-substituted α,β-unsaturated δ-lactones: application to the synthesis of styryllactones
  作者：Joel M Harris、George A O’Doherty

  DOI：10.1016/s0040-4039(99)02050-x

  日期：2000.1

  A flexible enantioselective synthesis of highly functionalized 5-substituted α,β-unsaturated δ-lactones has been achieved by applying the Sharpless catalytic asymmetric dihydroxylation to vinylfuran as the key step. The resulting diols are produced in high enantio excess and can be stereoselectively transformed into differentially protected δ-lactones through a short reaction sequence.

  通过对乙烯基呋喃进行Sharpless催化不对称二羟基化反应作为关键步骤，已经实现了高度官能化的5个取代的α，β-不饱和δ-内酯的柔性对映选择性合成。所产生的二醇以高对映体过量产生，并且可以通过短的反应序列立体选择性地转化为差异保护的δ-内酯。
• Syntheses of <scp>d</scp>- and <scp>l</scp>-Mannose, Gulose, and Talose via Diastereoselective and Enantioselective Dihydroxylation Reactions
  作者：Joel M. Harris、Mark D. Keranen、George A. O'Doherty

  DOI：10.1021/jo990410+

  日期：1999.4.1
• Syntheses of four d- and l-hexoses via diastereoselective and enantioselective dihydroxylation reactions
  作者：Joel M. Harris、Mark D. Keränen、Hang Nguyen、Victor G. Young、George A. O'Doherty

  DOI：10.1016/s0008-6215(00)00031-8

  日期：2000.8

  An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols call be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-delta-lactones were synthesized in eight steps and similar to 20% overall yield from furfural. (C) 2000 Elsevier Science Ltd. All rights reserved.