<(6-deoxy-α-L-galactopyranosyl)-(1->3)-<(β-D-galactopyranosyl)-(1->4)>-1,5-anhydro-2-deoxy-D-arabino-hex-1-enopyranose | 144092-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <(6-deoxy-α-L-galactopyranosyl)-(1->3)-<(β-D-galactopyranosyl)-(1->4)>-1,5-anhydro-2-deoxy-D-arabino-hex-1-enopyranose
• 英文别名: Lewis glucal
• CAS: 144092-27-3
• 化学式: C₁₈H₃₀O₁₃
• 分子量: 454.428
• InChiKey: ZMMMYHLCASWHEC-SEROXMGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.71
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  207.99
• 氢给体数：
  8.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  Acetic acid (3aS,4R,6S,7R,7aS)-4-acetoxymethyl-6-[(2R,3S,4R)-2-acetoxymethyl-4-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-3-yloxy]-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 <(6-deoxy-α-L-galactopyranosyl)-(1->3)-<(β-D-galactopyranosyl)-(1->4)>-1,5-anhydro-2-deoxy-D-arabino-hex-1-enopyranose
  参考文献：
  名称：

  Application of Glycals to the Synthesis of Oligosaccharides: Convergent Total Syntheses of the Lewis X Trisaccharide Sialyl Lewis X Antigenic Determinant and Higher Congeners

  摘要：

  Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLe(x) tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation-rearrangement step allows for the use of minimally protected glycosides as the glycosyl accepters. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Le(x) glycal.

  DOI：

  10.1021/ja00112a007