1-O-benzoyl-6-O-tert-butyldimethylsilyl-3-O-ethoxycarbonyl-α-D-mannopyranose | 222986-52-9

• 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: 1-O-benzoyl-6-O-tert-butyldimethylsilyl-3-O-ethoxycarbonyl-α-D-mannopyranose
• 英文别名: [(2R,3S,4R,5S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-ethoxycarbonyloxy-3,4-dihydroxyoxan-2-yl] benzoate
• CAS: 222986-52-9
• 化学式: C₂₂H₃₄O₉Si
• 分子量: 470.592
• InChiKey: RTJNDCLCXKDIRF-BFMVXSJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  原乙酸三甲酯 、 1-O-benzoyl-6-O-tert-butyldimethylsilyl-3-O-ethoxycarbonyl-α-D-mannopyranose 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以60%的产率得到2-O-acetyl-1-O-benzoyl-3-O-ethoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-mannopyranose
  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 4-二甲氨基吡啶 吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 15.5h， 生成 1-O-benzoyl-6-O-tert-butyldimethylsilyl-3-O-ethoxycarbonyl-α-D-mannopyranose
  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