allyl 2-acetamido-2-deoxy-6-O-p-toluenesulphonyl-α,β-D-glucopyranoside | 191925-47-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-2-deoxy-6-O-p-toluenesulphonyl-α,β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R)-5-acetamido-3,4-dihydroxy-6-prop-2-enoxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 191925-47-0
• 化学式: C₁₈H₂₅NO₈S
• 分子量: 415.464
• InChiKey: YHHUWVNGSJOGES-XNIMBYMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-乙基苄胺 、 allyl 2-acetamido-2-deoxy-6-O-p-toluenesulphonyl-α,β-D-glucopyranoside 反应 16.0h， 以58%的产率得到allyl 2-acetamido-6-(N-benzyl-N-ethyl)amino-2,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Potential HIV protease inhibitors: Preparation of di-N-alkylated 2-, 6-, and 2,6-aminodeoxy-derivatives of d-glucose by direct displacement and by a novel reductive-alkylation procedure

  摘要：

  Glucose derivatives carrying branched lipophilic groups at the 2-, 6-, and 2,6-positions were required for biological testing as inhibitors of the protease produced by the human immunodeficiency virus. The synthesis of (N-benzyl-N-ethyl)-2-, 6- and 2,6-diaminodeoxy-D-glucose derivatives is described. The 2-tert-amino group was introduced by a two-step reductive alkylation procedure. The novel tertiary aminosugar, 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-D-glucose, was made via direct substitution of the sulphonate group in allyl 2-acetamido-2-deoxy-6-O-tosyl-D-glucopyranoside with N-benzylethylamine. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00039-6
• 作为产物：
  描述：

  D-GlcNAc 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 allyl 2-acetamido-2-deoxy-6-O-p-toluenesulphonyl-α,β-D-glucopyranoside
  参考文献：
  名称：

  Potential HIV protease inhibitors: Preparation of di-N-alkylated 2-, 6-, and 2,6-aminodeoxy-derivatives of d-glucose by direct displacement and by a novel reductive-alkylation procedure

  摘要：

  Glucose derivatives carrying branched lipophilic groups at the 2-, 6-, and 2,6-positions were required for biological testing as inhibitors of the protease produced by the human immunodeficiency virus. The synthesis of (N-benzyl-N-ethyl)-2-, 6- and 2,6-diaminodeoxy-D-glucose derivatives is described. The 2-tert-amino group was introduced by a two-step reductive alkylation procedure. The novel tertiary aminosugar, 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-D-glucose, was made via direct substitution of the sulphonate group in allyl 2-acetamido-2-deoxy-6-O-tosyl-D-glucopyranoside with N-benzylethylamine. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00039-6

文献信息

• Potential HIV protease inhibitors: Preparation of di-N-alkylated 2-, 6-, and 2,6-aminodeoxy-derivatives of d-glucose by direct displacement and by a novel reductive-alkylation procedure
  作者：Jiaqiang Cai、Bruce E. Davison、C.Robin Ganellin、Suvit Thaisrivongs、Keith S. Wibley

  DOI：10.1016/s0008-6215(97)00039-6

  日期：1997.5

  Glucose derivatives carrying branched lipophilic groups at the 2-, 6-, and 2,6-positions were required for biological testing as inhibitors of the protease produced by the human immunodeficiency virus. The synthesis of (N-benzyl-N-ethyl)-2-, 6- and 2,6-diaminodeoxy-D-glucose derivatives is described. The 2-tert-amino group was introduced by a two-step reductive alkylation procedure. The novel tertiary aminosugar, 2,6-di-(N-benzyl-N-ethyl)amino-2,6-dideoxy-D-glucose, was made via direct substitution of the sulphonate group in allyl 2-acetamido-2-deoxy-6-O-tosyl-D-glucopyranoside with N-benzylethylamine. (C) 1997 Elsevier Science Ltd.