5-aminopentyl α-L-fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)-2-deoxy-2-acetoamido-β-D-galactopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside | 1363157-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-aminopentyl α-L-fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)-2-deoxy-2-acetoamido-β-D-galactopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
• 英文别名: 5-aminopentyl (α-L-fucopyranosyl)-(1->2)-(β-D-galactopyranosyl)-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
• CAS: 1363157-98-5
• 化学式: C₃₇H₆₆N₂O₂₅
• 分子量: 938.929
• InChiKey: LTXIKJOJQWRVJN-USAJWOLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.6
• 重原子数：
  64.0
• 可旋转键数：
  19.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  430.64
• 氢给体数：
  16.0
• 氢受体数：
  26.0

反应信息

• 作为产物：
  描述：

  N-benzyloxycarbonyl-5-aminopentyl (3,4-di-O-acetyl-2-O-benzoyl-α-L-fucopyranosyl)-(1→2)-(4,6-di-O-benzyl-β-D-galactopyranosyl)-(1→3)-(4,6-di-O-benzyl-2-deoxy-2-trichloracetamido-β-D-glucopyranosyl)-(1→3)-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3-di-O-benzoyl-6-O-benzyl-β-D-glucopyranoside 在 sodium methylate 、 5%-palladium/activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以46%的产率得到5-aminopentyl α-L-fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)-2-deoxy-2-acetoamido-β-D-galactopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
  参考文献：
  名称：

  Automated Glycan Assembly of Complex Oligosaccharides Related to Blood Group Determinants

  摘要：

  Lactotetraosyl (Lc4) and neo-lactotetraosyl (nLc4) are backbones that are common to many glycans. Using automated glycan assembly, these common core structures were constructed and elaborated to access synthetically challenging glycans of biological relevance. The incorporation of alpha-fucoses is demonstrated for H-type I and II; alpha(1,3)-galactose epitopes were prepared, and the pentasaccharide HNK-1 required incorporation of a 3-O-sulfate. In addition to preparing the target structures, essential insights were gained regarding the relationships of glycosylating agents and nucleophiles as well as the linker stability.

  DOI：

  10.1021/acs.joc.6b00554

文献信息

• Acyl and Silyl Group Effects in Reactivity-Based One-Pot Glycosylation: Synthesis of Embryonic Stem Cell Surface Carbohydrates Lc₄ and IV²Fuc-Lc₄
  作者：Yun Hsu、Xin-An Lu、Medel Manuel L. Zulueta、Chih-Ming Tsai、Kuo-I Lin、Shang-Cheng Hung、Chi-Huey Wong

  DOI：10.1021/ja300284x

  日期：2012.3.14

  Relative reactivity evaluations showed the graded arming of toluenyl thioglucosides by variously positioned silyl groups but not by their acyl counterparts. These findings were applied in reactivity-based one-pot assembly of linker-attached Lc(4) and IV(2)Fuc-Lc(4), which are components of human embryonic stem cell surface. The sugar-galectin-1 binding was also examined.