allyl (3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside | 1358951-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: allyl (3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
• CAS: 1358951-16-2
• 化学式: C₃₁H₃₄N₆O₁₀
• 分子量: 650.645
• InChiKey: HBFMRLMLNSOETE-CKEYEHPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  197.66
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  allyl (3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到allyl (2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->3)-2-azido-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
• 作为产物：
  描述：

  phenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside 在 bismuth(lll) trifluoromethanesulfonate 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 allyl (3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1->3)-2-azido-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