(2R,3R)-2-(tert-butyldimethylsilanyloxymethyl)-6-oxo-3,6-dihydro-2H-pyran-3-yl ethyl carbonate | 260426-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,3R)-2-(tert-butyldimethylsilanyloxymethyl)-6-oxo-3,6-dihydro-2H-pyran-3-yl ethyl carbonate
• 英文别名: [(2R,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-oxo-2,3-dihydropyran-3-yl] ethyl carbonate
• CAS: 260426-06-0
• 化学式: C₁₅H₂₆O₆Si
• 分子量: 330.453
• InChiKey: FUWAUXUZASLLLZ-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(tert-butyldimethylsilanyloxymethyl)-6-oxo-3,6-dihydro-2H-pyran-3-yl ethyl carbonate 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 3.0h， 以79%的产率得到(2R,3R,4R,5R)-6-(tert-butyldimethylsilanyloxymethyl)-4,5-dihydroxy-6-oxotetrahydropyran-3-yl ethyl carbonate
  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：

  (2R)-2-tert-butyldimethylsilanyloxymethyl-6-hydroxy-6H-pyran-3-one 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.33h， 生成 (2R,3R)-2-(tert-butyldimethylsilanyloxymethyl)-6-oxo-3,6-dihydro-2H-pyran-3-yl ethyl carbonate
  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

• 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 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.