methyl [2-methyl 5-acetamido-4-(1,4-dioxa-8-azaspiro[4,5]dec-8-yl)-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid]onate | 1112860-23-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [2-methyl 5-acetamido-4-(1,4-dioxa-8-azaspiro[4,5]dec-8-yl)-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-methoxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 1112860-23-7
• 化学式: C₂₆H₄₀N₂O₁₃
• 分子量: 588.609
• InChiKey: MZORQAKPMRMQDH-SFOUIMQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  175
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  甲醇 、 methyl (2S,4S,5R,6R)-5-acetamido-4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-hydroxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 三氟甲磺酸酐 、 二苯基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到methyl [2-methyl 5-acetamido-4-(1,4-dioxa-8-azaspiro[4,5]dec-8-yl)-7,8,9-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
  参考文献：
  名称：

  Efficient Dehydrative Sialylation of C-4-Aminated Sialyl-Hemiketal Donors with Ph₂SO/Tf₂O

  摘要：

  An efficient approach to the dehydrative sialylation of various substrates with C-4-aminated sialyl-hemiketal donors by using the reagent combination of diphenyl sulfoxide and triflic anhydride is reported. By using a C-4-hindered non-nucleophilic amine auxiliary, excellent yields and high alpha-stereoselectivities were obtained for coupling with a wide range of primary and secondary acceptors.

  DOI：

  10.1021/jo802396a