2-deoxy-3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosyl-(1->O)-N-(1-oxopentadecyl)-L-serine methyl ester | 1327260-10-5

• 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: 2-deoxy-3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosyl-(1->O)-N-(1-oxopentadecyl)-L-serine methyl ester
• 英文别名: methyl (2S)-3-[(2S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-(pentadecanoylamino)propanoate
• CAS: 1327260-10-5
• 化学式: C₄₆H₆₅NO₈
• 分子量: 760.024
• InChiKey: IJGPILCAZQPGRK-YJNXVKQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  55
• 可旋转键数：
  29
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl (2S)-3-hydroxy-2-(pentadecanoylamino)propanoate 、 3,4,6-三邻苄基半乳醛 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 2-deoxy-3,4,6-tri-O-benzyl-β-D-lyxo-hexopyranosyl-(1->O)-N-(1-oxopentadecyl)-L-serine methyl ester 、 2-deoxy-3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosyl-(1->O)-N-(1-oxopentadecyl)-L-serine methyl ester
  参考文献：
  名称：

  Stereoselective glycosylation of endo-glycals by microwave- and AlCl3-assisted catalysis

  摘要：

  alpha-2-Deoxyglycosides were synthesized in good to excellent yields by microwave-assisted reaction of endo-glycals with various O-nucleophiles in the presence of catalytic amount of AlCl3. These glycosyl additions occurred with high alpha-stereoselectivity and were complete in 5-35 min in 65-93% yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.124

文献信息

• Stereoselective glycosylation of endo-glycals by microwave- and AlCl3-assisted catalysis
  作者：Hui-Chang Lin、Jia-Fu Pan、Yen-Bo Chen、Zi-Ping Lin、Chun-Hung Lin

  DOI：10.1016/j.tet.2011.05.124

  日期：2011.8

  alpha-2-Deoxyglycosides were synthesized in good to excellent yields by microwave-assisted reaction of endo-glycals with various O-nucleophiles in the presence of catalytic amount of AlCl3. These glycosyl additions occurred with high alpha-stereoselectivity and were complete in 5-35 min in 65-93% yield. (C) 2011 Elsevier Ltd. All rights reserved.