methyl 2,3,4,6-tetra-O-acetyl-1-C-methyl-α-D-glucopyranoside | 83615-55-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4,6-tetra-O-acetyl-1-C-methyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-methoxy-6-methyloxan-2-yl]methyl acetate
• CAS: 83615-55-8
• 化学式: C₁₆H₂₄O₁₀
• 分子量: 376.361
• InChiKey: HOBFLWNTGKGVKB-LJIZCISZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-acetyl-1-C-methyl-α-D-glucopyranoside 、 methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose 在 4 A molecular sieve 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以30.1%的产率得到methyl O-(1'-C-methyl-2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->6)-2,3,4-tri-O-acetyl-α-D-glucoside
  参考文献：
  名称：

  A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides

  摘要：

  Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded alpha -stereoselectively and furnished the corresponding 1'-C-alkyl-alpha -disaccharides in 71-90% yields. The O-transglycosidations from the benzylated and acetylated methyl I-C-methyl-or-hexopyranosides to the corresponding 1'-C-methyl-alpha -O-disaccharides were also examined, respectively. These transglycosidations took place on alpha -stereoselectivity and provided the 1'-C-methyl-alpha -O-disaccharides as the sole products, implying that no neighboring group participation occured in the reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00321-0
• 作为产物：
  描述：

  methyl 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-D-glucopyranoside 在 palladium dihydroxide 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl 2,3,4,6-tetra-O-acetyl-1-C-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides

  摘要：

  Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded alpha -stereoselectively and furnished the corresponding 1'-C-alkyl-alpha -disaccharides in 71-90% yields. The O-transglycosidations from the benzylated and acetylated methyl I-C-methyl-or-hexopyranosides to the corresponding 1'-C-methyl-alpha -O-disaccharides were also examined, respectively. These transglycosidations took place on alpha -stereoselectivity and provided the 1'-C-methyl-alpha -O-disaccharides as the sole products, implying that no neighboring group participation occured in the reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00321-0