methyl (benzyl 2,3-di-O-benzoyl-β-D-glucopyranoside)uronate | 208389-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (benzyl 2,3-di-O-benzoyl-β-D-glucopyranoside)uronate
• 英文别名: methyl (2S,3S,4S,5R,6R)-4,5-dibenzoyloxy-3-hydroxy-6-phenylmethoxyoxane-2-carboxylate
• CAS: 208389-99-5
• 化学式: C₂₈H₂₆O₉
• 分子量: 506.509
• InChiKey: FMSJKZTYHYEFMP-SXFUUEIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (benzyl 2,3-di-O-benzoyl-β-D-glucopyranoside)uronate 在 二氯二茂锆 、 sodium methylate 、 silver perchlorate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 methyl [benzyl O-(2-azido-3-O-benzyl-2-deoxy-6-O-sulfonato-α-D-glucopyranosyl)-(1-4)-β-D-glucopyranoside]uronate
  参考文献：
  名称：

  Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions

  摘要：

  A variety of sulfo-protected monosaccharide donors and acceptors were investigated in glycosylation reactions. Trifluoro-ethylsulfonate (SO3TFE) group was compatible with a wide range of activation conditions commonly used with fluoride, imidate, and sulfide donors. In addition, the influence of a SO3TFE group, at the critical 2-position in glycosyl donor, on the stereoselectivity of the glycosylation reaction was studied. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.131
• 作为产物：
  描述：

  苄基beta-D-吡喃葡糖苷酸甲酯三乙酸酯 在 sodium methylate 、 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 methyl (benzyl 2,3-di-O-benzoyl-β-D-glucopyranoside)uronate
  参考文献：
  名称：

  Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions

  摘要：

  A variety of sulfo-protected monosaccharide donors and acceptors were investigated in glycosylation reactions. Trifluoro-ethylsulfonate (SO3TFE) group was compatible with a wide range of activation conditions commonly used with fluoride, imidate, and sulfide donors. In addition, the influence of a SO3TFE group, at the critical 2-position in glycosyl donor, on the stereoselectivity of the glycosylation reaction was studied. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.131

文献信息

• Regio- and Stereoselective Synthesis of β-<scp>d</scp>-Gluco-, α-<scp>l</scp>-Ido-, and α-<scp>l</scp>-Altropyranosiduronic Acids from Δ⁴-Uronates
  作者：Hélène G. Bazin、Michael W. Wolff、Robert J. Linhardt

  DOI：10.1021/jo981477k

  日期：1999.1.1

  The stereoselective synthesis of beta-D-glucopyranosiduronic, alpha-L-idopyranosiduronic, and alpha-L-altropyranosiduronic acids has been performed from different Delta(4)-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using boranetetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding alpha-L C-4 ketopyranosides adopting the C-1(4) chair conformation. Hydride reduction afforded the alpha-L-idopyranosiduronic or the alpha-L-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.
• Oxazolidinone Protected 2-Amino-2-deoxy-<scp>d</scp>-glucose Derivatives as Versatile Intermediates in Stereoselective Oligosaccharide Synthesis and the Formation of α-Linked Glycosides
  作者：Kamel Benakli、Congxiang Zha、Robert J. Kerns

  DOI：10.1021/ja0162109

  日期：2001.9.1
• Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions
  作者：Nathalie A. Karst、Tasneem F. Islam、Fikri Y. Avci、Robert J. Linhardt

  DOI：10.1016/j.tetlet.2004.06.131

  日期：2004.8

  A variety of sulfo-protected monosaccharide donors and acceptors were investigated in glycosylation reactions. Trifluoro-ethylsulfonate (SO3TFE) group was compatible with a wide range of activation conditions commonly used with fluoride, imidate, and sulfide donors. In addition, the influence of a SO3TFE group, at the critical 2-position in glycosyl donor, on the stereoselectivity of the glycosylation reaction was studied. (C) 2004 Elsevier Ltd. All rights reserved.