(2R,3S,4S,5R,6R)-2-(乙酰氧基甲基)-6-硫代氨基甲酰四氢-2H-吡喃-3,4,5-三基三乙酸酯 | 358738-47-3

• 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
• 中文名称: (2R,3S,4S,5R,6R)-2-(乙酰氧基甲基)-6-硫代氨基甲酰四氢-2H-吡喃-3,4,5-三基三乙酸酯
• 英文名称: C-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)thioformamide
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-carbamothioyloxan-2-yl]methyl acetate
• CAS: 358738-47-3
• 化学式: C₁₅H₂₁NO₉S
• 分子量: 391.399
• InChiKey: YQAZWCLGEQWBOY-MBJXGIAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-2-(乙酰氧基甲基)-6-硫代氨基甲酰四氢-2H-吡喃-3,4,5-三基三乙酸酯 在 三乙胺 作用下， 以 甲醇 为溶剂， 以87%的产率得到C-(β-D-galactopyranosyl)thioformamide
  参考文献：
  名称：

  Preparation of 3,5-bis-(β- d -glycopyranosyl)-1,2,4-thiadiazoles from C -(β- d -glycopyranosyl)thioformamides

  摘要：

  Acylated C-glycopyranosyl thioformamides of D-gluco, D-galacto, and D-xylo configuration were obtained by treating the corresponding glycosyl cyanides with hydrogen sulfide in the presence of triethylamine. The thioformamides gave 3,5-bis-(beta -D-glycopyranosyl)-1,2,4-thiadiazoles in reactions with potassium bromate and sodium dithionite in dichloromethane-water biphasic solvent mixture. Deprotected derivatives were prepared by Zemplen deacylation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00444-6
• 作为产物：
  描述：

  (2R,3S,4R,5S,6S)-2-(乙酰氧基甲基)-6-氰基四氢-2H-吡喃-3,4,5-三基三乙酸酯 在 硫化氢 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以84%的产率得到(2R,3S,4S,5R,6R)-2-(乙酰氧基甲基)-6-硫代氨基甲酰四氢-2H-吡喃-3,4,5-三基三乙酸酯
  参考文献：
  名称：

  Preparation of 3,5-bis-(β- d -glycopyranosyl)-1,2,4-thiadiazoles from C -(β- d -glycopyranosyl)thioformamides

  摘要：

  Acylated C-glycopyranosyl thioformamides of D-gluco, D-galacto, and D-xylo configuration were obtained by treating the corresponding glycosyl cyanides with hydrogen sulfide in the presence of triethylamine. The thioformamides gave 3,5-bis-(beta -D-glycopyranosyl)-1,2,4-thiadiazoles in reactions with potassium bromate and sodium dithionite in dichloromethane-water biphasic solvent mixture. Deprotected derivatives were prepared by Zemplen deacylation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00444-6