3,4,6-tri-O-acetyl-2-O-methoxycarbonyl-D-galactopyranosyl trichloroacetimidate | 1358951-21-9

• 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: 3,4,6-tri-O-acetyl-2-O-methoxycarbonyl-D-galactopyranosyl trichloroacetimidate
• CAS: 1358951-21-9
• 化学式: C₁₆H₂₀Cl₃NO₁₁
• 分子量: 508.694
• InChiKey: WJLLMABABNLPDU-YMWOCUMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  156.74
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-O-methoxycarbonyl-D-galactopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 乙酸酐 、 铜 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 8.25h， 生成 allyl (3,4,6-tri-O-acetyl-2-O-methoxycarbonyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the trisaccharide outer core fragment of Burkholderia cepacia pv. vietnamiensis lipooligosaccharide

  摘要：

  The synthesis of beta-Gal-(1 -> 3)-alpha-GalNAc-(1 -> 3)-beta-GalNAc allyl trisaccharide as the outer core fragment of Burkholderia cepacia pv. vietnamiensis lipooligosaccharide was accomplished through a concise, optimized, multi-step synthesis, having as key steps three glycosylations, that were in-depth studied performing them under several conditions. The target trisaccharide was designed with an allyl aglycone in order to open a future access to the conjugation with an immunogenic protein en route to the development of a synthetic neoglycoconjugate vaccine against this Burkholderia pathogen. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.12.007