methyl 4-O-benzyl-α-L-galactopyranoside | 1219031-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzyl-α-L-galactopyranoside
• CAS: 1219031-17-0
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: NJIGNMLBFITYSP-QSLWVIQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  88.38
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  甲醇 、 在 三氟甲磺酸三甲基硅酯 作用下， 反应 48.0h， 以0.15 g的产率得到methyl 4-O-benzyl-α-L-galactopyranoside
  参考文献：
  名称：

  Highly Stereoselective de Novo Synthesis of l-Hexoses

  摘要：

  An efficient and general de novo synthetic route to enantiomerically pure L-hexoses has been accomplished starting from the heterocyclic homologating agent 5,6-dihydro-1,4-dithiin-2-yl[(4-methoxybentyl)oxy]methane and methyl alpha,beta-isopropylidene-L-glycerate. The sugar scaffold was constructed by an acid-catalyzed domino reaction, which enabled selective preparation of either methyl 2,3-dideoxy-alpha-L-threohex-2-enopyranosides or 1,6-anhydro-2,3-dideoxy-beta-L-threo-hex-2-enopyranose as key intermediates. The subsequent double bond functionalization by syn or anti dihydroxylation reactions allowed introduction of the remaining stereogenic centers, leading to desired orthogonally protected L-hexopyranosides with a high degree of diastereoselectivity and with very good overall yields. These and previous results (based on the use of the corresponding L-erythro epimers) contribute to make our approach general and place it among the few methods able to synthesize the whole series of the rare L-hexoses.

  DOI：

  10.1021/jo100077k