Benzyl-2-acetamido-4-azido-2,4-didesoxy-3,6-di-O-dibenzoyl-α-D-galactopyranosid | 155136-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl-2-acetamido-4-azido-2,4-didesoxy-3,6-di-O-dibenzoyl-α-D-galactopyranosid
• CAS: 155136-04-2
• 化学式: C₂₉H₂₈N₄O₇
• 分子量: 544.564
• InChiKey: RWYLWSKNPRZEKX-XGBSQYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  148.92
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Benzyl-2-acetamido-4-azido-2,4-didesoxy-3,6-di-O-dibenzoyl-α-D-galactopyranosid 在 sodium ethanolate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到Benzyl-2-acetamido-4-azido-2,4-didesoxy-α-D-galactopyranosid
  参考文献：
  名称：

  Synthese von 2-acetamido-1,4-imino-1,2,4-tridesoxy-d- galaktitol und kompetitive Inhibition der humanen lysosomalen β-hexosaminidase A

  摘要：

  The synthesis of 2-acetamido-1,4-imino-1,2,4-trideoxy-D-galactitol (1; 2-acetamido-4-amino-1,4-anhydro-2,4-dideoxy-D-galactitol) by two different routes starting from 2-acetamido-2-deoxy-D-glucose is described. Compound 1 is a competitive inhibitor of human lysosomal beta-hexosaminidase A with K-i values of 18 mu M (beta-subunit) and 220 mu M (alpha-subunit). Similiar properties were found for the already known 2-acetamido-2-deoxy-D-gluco-hydroximo-1,4-lactone.

  DOI：

  10.1016/0008-6215(93)84151-u
• 作为产物：
  描述：

  Benzyl-2-acetamido-3,6-di-O-benzoyl-2-desoxy-4-O-(trifluormethylsulfonyl)-α-D-glucopyranosid 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 Benzyl-2-acetamido-4-azido-2,4-didesoxy-3,6-di-O-dibenzoyl-α-D-galactopyranosid
  参考文献：
  名称：

  Synthese von 2-acetamido-1,4-imino-1,2,4-tridesoxy-d- galaktitol und kompetitive Inhibition der humanen lysosomalen β-hexosaminidase A

  摘要：

  The synthesis of 2-acetamido-1,4-imino-1,2,4-trideoxy-D-galactitol (1; 2-acetamido-4-amino-1,4-anhydro-2,4-dideoxy-D-galactitol) by two different routes starting from 2-acetamido-2-deoxy-D-glucose is described. Compound 1 is a competitive inhibitor of human lysosomal beta-hexosaminidase A with K-i values of 18 mu M (beta-subunit) and 220 mu M (alpha-subunit). Similiar properties were found for the already known 2-acetamido-2-deoxy-D-gluco-hydroximo-1,4-lactone.

  DOI：

  10.1016/0008-6215(93)84151-u