(2S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl pivalate | 222986-43-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl pivalate
• 英文别名: [(2R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxo-2H-pyran-2-yl] 2,2-dimethylpropanoate
• CAS: 222986-43-8
• 化学式: C₁₇H₃₀O₅Si
• 分子量: 342.508
• InChiKey: UVTRIAYQUPIASJ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 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 pivalate 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到(2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl pivalate
  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 pivalate
  参考文献：
  名称：

  Syntheses of d- and l-Mannose, Gulose, and Talose via Diastereoselective and Enantioselective Dihydroxylation Reactions

  摘要：

  DOI：

  10.1021/jo990410+

文献信息

• 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
• Allylic substitution on the pyran ring
  作者：Tomonori Hyodo、Yuji Katayama、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2009.03.018

  日期：2009.7

  Allylic substitution of pyrans 10 and 15 possessing the picolinoxy leaving group with several alkyl and aryl copper reagents derived from RMgBr and CUBr center dot Me2S was studied. First, reaction of 10 with three copper reagents derived from EtMgBr (2 equiv) and different equivalents of CuBr center dot Me2S (2, 1, and 0.5 equiv, respectively) was examined in THF at -20 degrees C for 1 h to afford anti S(N)2' product 16a in high yields in all cases. Under these reaction conditions Me, i-Pr, Ph, o-MeC6H4, and o-MeOC6H4 were installed on the pyran ring of 10 successfully. Similar results were also obtained with pyran 15. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.