1-O-pivaloyl-6-O-tert-butyldimethylsilyl-α-D-gulopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-pivaloyl-6-O-tert-butyldimethylsilyl-α-D-gulopyranose
• 英文别名: TBDMS(-6)Gul(a)-O-pivaloyl；[(2R,3R,4R,5R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] 2,2-dimethylpropanoate
• 化学式: C₁₇H₃₄O₇Si
• 分子量: 378.538
• InChiKey: HLIXRKQKMDOIAH-XVIXHAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R)-2-tert-butyldimethylsilanyloxymethyl-6-hydroxy-6H-pyran-3-one 在 4-二甲氨基吡啶 甲醇 、 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 N-甲基吗啉氧化物 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 36.5h， 生成 1-O-pivaloyl-6-O-tert-butyldimethylsilyl-α-D-gulopyranose
  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

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
• 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.