(+)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside | 73024-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
• CAS: 73024-74-5
• 化学式: C₁₄H₂₁NO₉
• 分子量: 347.322
• InChiKey: RCYLXESGSHGRBI-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.37
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  137.46
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (+)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 在 三氟化硼乙醚 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-[N-α-(9-fluorenylmethoxycarbonyl)-l-thiazolidine-4-carbonyl]amino-β-D-glucopyranosyl-(1→4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl acetate
  参考文献：
  名称：

  Enzymatic polymerization to an alternating N-l-cysteinyl chitin derivative: a novel class of multivalent glycopeptidomimetics

  摘要：

  A novel chitin derivative with an alternating N-L-cysteinyl group was successfully prepared. The precursor chitin derivative with an alternating N-L-thioprolinyl group could be obtained via chitinase-catalyzed polymerization of the N'-L-thioprolinyl chitobiose oxazoline derivative as a transition state analog substrate monomer under weak alkaline conditions. Conversion of the L-thioprolinyl group to an L-cysteinyl group in the product chitin derivative proceeded in a dose-dependent manner by methoxyamine hydrochloride, and the reaction could be completed almost quantitatively. The obtained chitin derivative is a uniformly amino acid-branching polysaccharide, which is categorized into a novel class of multivalent glycopeptidomimetics. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.05.009