methyl 3,4-di-O-acetyl-2-benzamido-2,6-dideoxy-α-D-glucopyranoside-6-N-butylsulfonamide | 497178-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-acetyl-2-benzamido-2,6-dideoxy-α-D-glucopyranoside-6-N-butylsulfonamide
• 英文别名: [(2S,3S,4R,5R,6S)-4-acetyloxy-5-benzamido-2-(butylsulfamoylmethyl)-6-methoxyoxan-3-yl] acetate
• CAS: 497178-06-0
• 化学式: C₂₂H₃₂N₂O₉S
• 分子量: 500.57
• InChiKey: LKKZCXKDEVJDPK-DOSYZEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-acetyl-2-benzamido-2,6-dideoxy-α-D-glucopyranoside-6-N-butylsulfonamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到methyl 2-benzamido-2,6-dideoxy-α-D-glucopyranoside-6-N-butylsulfonamide
  参考文献：
  名称：

  New N-alkylsulfonamides and alkyl sulfonates derived from 6-C-sulfosugars

  摘要：

  Protected 6-C-sulfosugars have been transformed into alkyl sulfonates and N-alkylsulfonamides, including a pseudo-disaccharide with a 6 to 6'-sulfonamide linkage. The method involves the oxidation of 6-thioacetate sugar derivatives to 6-C-sulfosugars, and their transformation into sulfonyl chlorides using SO2O2 in anhydrous CH2O2 followed by in situ coupling with nucleophiles in the presence of an excess of base. Sulfonylation through phase-transfer conditions has proved to be suitable for the synthesis of the pseudo-disaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00874-8
• 作为产物：
  描述：

  methyl 3,4-di-O-acetyl-6-S-acetyl-2-benzamido-2-deoxy-6-thio-α-D-glucopyranoside 在 磺酰氯 、 4 A molecular sieve 、 双氧水 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 methyl 3,4-di-O-acetyl-2-benzamido-2,6-dideoxy-α-D-glucopyranoside-6-N-butylsulfonamide
  参考文献：
  名称：

  New N-alkylsulfonamides and alkyl sulfonates derived from 6-C-sulfosugars

  摘要：

  Protected 6-C-sulfosugars have been transformed into alkyl sulfonates and N-alkylsulfonamides, including a pseudo-disaccharide with a 6 to 6'-sulfonamide linkage. The method involves the oxidation of 6-thioacetate sugar derivatives to 6-C-sulfosugars, and their transformation into sulfonyl chlorides using SO2O2 in anhydrous CH2O2 followed by in situ coupling with nucleophiles in the presence of an excess of base. Sulfonylation through phase-transfer conditions has proved to be suitable for the synthesis of the pseudo-disaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00874-8