methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside | 1138457-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside
• CAS: 1138457-34-7
• 化学式: C₃₆H₄₁NO₁₆
• 分子量: 743.719
• InChiKey: PSJWPDCKXKKQCM-IOWGKIEZSA-N

物化性质

• 沸点：
  793.8±60.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  53.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  208.96
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  dodecyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 、 methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)]-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside
  参考文献：
  名称：

  Pre-activation of fully acetylated dodecyl thioglycosides with BSP–Tf2O led to efficient glycosylation at low temperature

  摘要：

  Fully acetylated dodecyl thioglycosides were found to be useful as glycosyl donors by activation with 1-benzenesulfinyl piperidine (BSP) and triflic anhydride (Tf2O) at -78 degrees C. The glycosyl acceptor was added to the reaction mixture at the same temperature to furnish various disaccharide, including the protected Lewis a (Le(a)) trisaccharide, in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.11.008
• 作为产物：
  描述：

  methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-glucopyranoside 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以72%的产率得到methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside
  参考文献：
  名称：

  Pre-activation of fully acetylated dodecyl thioglycosides with BSP–Tf2O led to efficient glycosylation at low temperature

  摘要：

  Fully acetylated dodecyl thioglycosides were found to be useful as glycosyl donors by activation with 1-benzenesulfinyl piperidine (BSP) and triflic anhydride (Tf2O) at -78 degrees C. The glycosyl acceptor was added to the reaction mixture at the same temperature to furnish various disaccharide, including the protected Lewis a (Le(a)) trisaccharide, in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.11.008