methyl (4,6-di-O-acetyl-2,3-O-carbonyl-α-D-glucopyranosyl)-(1.6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 1380234-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4,6-di-O-acetyl-2,3-O-carbonyl-α-D-glucopyranosyl)-(1.6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: [(3aR,4R,6R,7R,7aS)-7-acetyloxy-4-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-2-oxo-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]methyl acetate
• CAS: 1380234-14-9
• 化学式: C₃₉H₄₄O₁₄
• 分子量: 736.77
• InChiKey: VECCSYBEZZDYQI-HJNYCSSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  53
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl (4,6-di-O-acetyl-2,3-O-carbonyl-α-D-glucopyranosyl)-(1.6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 以 二氯甲烷 为溶剂， 生成 methyl (4,6-di-O-acetyl-2,3-O-carbonyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Lewis Acids as α-Directing Additives in Glycosylations by Using 2,3-O-Carbonate-Protected Glucose and Galactose Thioglycoside Donors Based on Preactivation Protocol

  摘要：

  Catalytic or stoichiometric amounts of Lewis acids were found to be very effective a-directing additives in the stereoselective glycosylations of diverse 2,3-O-carbonate-protected glucose and galactose thioglycoside donors by preactivation protocol. The poor stereoselectivities of 4,6-di-O-acetyl-2,3-O-carbonate protected thioglycoside donors in glycosyl coupling reactions were greatly improved, and excellent alpha-stereoselectivities were achieved by the addition of 0.2 equiv of BF3 center dot OEt2. On the other hand, the beta-selectivities of 4,6-di-O-benzyl-2,3-O-carbonate-protected thioglucoside donor toward glycosylations were reversed completely to the alpha-selectivities by the use of 1 equiv of SnCl4, making the stereoselectivity controllable. Furthermore, the poor stereoselectivities of 4,6-di-O-benzyl-2,3-O-carbonate-protected thiogalactoside donor in glycosylations were also improved by using SnCl4 as additive.

  DOI：

  10.1021/jo3002084