allyl 2-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside | 191925-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• CAS: 191925-43-6
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: AWBSUJADSSDQBJ-RCQJKQRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  69.18
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 2-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 sodium tetrahydroborate 、 水 、 溶剂黄146 作用下， 反应 11.0h， 生成 allyl 2-(N-benzyl-N-ethyl)amino-2-deoxy-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：

  allyl 2-acetamido-2-deoxy-α,β-D-glucopyranoside 在 sodium hydroxide 、 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 152.0h， 生成 allyl 2-benzylamino-4,6-O-benzylidene-2-deoxy-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

文献信息

• <i>O</i>- and <i>N</i>-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts
  作者：Laura J. Ingram、Ahmed Desoky、Ahmed M. Ali、Scott D. Taylor

  DOI：10.1021/jo9014112

  日期：2009.9.4

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.