N,N-bis(2,4-dimethoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide | 1138026-22-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-bis(2,4-dimethoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[bis[(2,4-dimethoxyphenyl)methyl]amino]sulfanyloxan-2-yl]methyl acetate
• CAS: 1138026-22-8
• 化学式: C₃₂H₄₁NO₁₃S
• 分子量: 679.742
• InChiKey: FSRTYFLTHWLEGG-VJLURNNQSA-N

物化性质

• 熔点：
  143-144 °C
• 沸点：
  732.2±70.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  180
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N,N-bis(2,4-dimethoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide 在 potassium permanganate 、 copper(ll) sulfate pentahydrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 以17%的产率得到N,N-bis(2,4-dimethoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfonamide
  参考文献：
  名称：

  Synthesis of S-Glycosyl Primary Sulfonamides

  摘要：

  The synthesis of S-glycosyl sulfonamides wherein the primary sulfonamide functional group (-SO2NH2) is directly attached to the anomeric position of a carbohydrate moiety is reported. Our general approach consists of first introducing a thioacetate group at die anomeric center of a per-O-acetylated sugar derivative. From this follows formation of a glycosyl sulfenamide (sugar-SNR2), oxidation of the sulfenamide to give a glycosyl N-protected sulfonamide (sugar-SO2NR2), and removal of the sulfonamide protecting (R) group to yield a primary sulfonamide at the anomeric center (sugar-SO2NH2). A variety of mono- and disaccharide derivatives were synthesized using this new methodology.

  DOI：

  10.1021/jo9000367
• 作为产物：
  描述：

  双(2,4-二甲氧基苄基)胺 、 1-硫代-beta-D-葡萄糖五乙酸酯 在 溴代丙二酸二乙酯 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以79%的产率得到N,N-bis(2,4-dimethoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide
  参考文献：
  名称：

  Synthesis of S-Glycosyl Primary Sulfonamides

  摘要：

  The synthesis of S-glycosyl sulfonamides wherein the primary sulfonamide functional group (-SO2NH2) is directly attached to the anomeric position of a carbohydrate moiety is reported. Our general approach consists of first introducing a thioacetate group at die anomeric center of a per-O-acetylated sugar derivative. From this follows formation of a glycosyl sulfenamide (sugar-SNR2), oxidation of the sulfenamide to give a glycosyl N-protected sulfonamide (sugar-SO2NR2), and removal of the sulfonamide protecting (R) group to yield a primary sulfonamide at the anomeric center (sugar-SO2NH2). A variety of mono- and disaccharide derivatives were synthesized using this new methodology.

  DOI：

  10.1021/jo9000367