[4-Amino-5-((1S,2R,3S,4R)-1,2,3,4,5-pentahydroxy-pentyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetic acid ethyl ester | 911641-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [4-Amino-5-((1S,2R,3S,4R)-1,2,3,4,5-pentahydroxy-pentyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetic acid ethyl ester
• CAS: 911641-21-9
• 化学式: C₁₁H₂₀N₄O₇S
• 分子量: 352.368
• InChiKey: SWYHGWQKBMFJNJ-RSWFSCQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.24
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  184.18
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  [4-Amino-5-((1S,2R,3S,4R)-1,2,3,4,5-pentahydroxy-pentyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetic acid ethyl ester 、 乙酸酐 在 吡啶 作用下， 生成 4-amino-3-(1,2,3,4,5-penta-O-acetyl-D-galacto-pentitol-1-yl)-5-(ethoxycarbonylmethyl)thio-4H-1,2,4-triazole
  参考文献：
  名称：

  Microwave-Assisted Organic Synthesis of 3-(D-gluco- Pentitol-1-Yl)-1H-1,2,4-Triazole

  摘要：

  The condensation of D-glucono- and the D-galactono-1,5-lactone and thiocarbohydrazide to give 3-(D-alditol-1-yl)-4-amino-5-mercapto-1,2,4-triazoles 4 and 5 is accelerated by the use of microwave-assisted organic reaction (MAOS). The deamination and dethiolation of compound 4 to give 6 was also accelerated by the use of MAOS. Condensation of 4 and 5 with p-nitrobenzaldehyde afforded Schiff bases 8 and 9, respectively, within 4 min under microwave irradiation (MWI), whereas with ethyl chloroacetate the thioalkylated products 14 and 15 were obtained in 8 min. The structures of the synthesized compounds were confirmed by H-1 NMR, 2D NMR, and mass spectra.

  DOI：

  10.1080/15257770500544545
• 作为产物：
  描述：

  D-galactono-1,5-lactone 在 吡啶 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 0.13h， 生成 [4-Amino-5-((1S,2R,3S,4R)-1,2,3,4,5-pentahydroxy-pentyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetic acid ethyl ester
  参考文献：
  名称：

  Microwave-Assisted Organic Synthesis of 3-(D-gluco- Pentitol-1-Yl)-1H-1,2,4-Triazole

  摘要：

  The condensation of D-glucono- and the D-galactono-1,5-lactone and thiocarbohydrazide to give 3-(D-alditol-1-yl)-4-amino-5-mercapto-1,2,4-triazoles 4 and 5 is accelerated by the use of microwave-assisted organic reaction (MAOS). The deamination and dethiolation of compound 4 to give 6 was also accelerated by the use of MAOS. Condensation of 4 and 5 with p-nitrobenzaldehyde afforded Schiff bases 8 and 9, respectively, within 4 min under microwave irradiation (MWI), whereas with ethyl chloroacetate the thioalkylated products 14 and 15 were obtained in 8 min. The structures of the synthesized compounds were confirmed by H-1 NMR, 2D NMR, and mass spectra.

  DOI：

  10.1080/15257770500544545

文献信息

• MICROWAVE IRRADIATION FOR ACCELERATING THE SYNTHESIS OF ACYCLONUCLEOSIDES OF 1,2,4-TRIAZOLE
  作者：E. S. H. El Ashry、L. F. Awad、H. M. Abdel Hamid、A. I. Atta

  DOI：10.1081/ncn-200059975

  日期：2005.4.1

  The 3-(D-alditol-1-yl)-4-amino-5-mercapto- 1,2,4-triazoles 4 and 5 can be successfully prepared using microwave irradiation. Condensation of 4 and 5 with p-nitrobenzaldehyde afforded Schiff bases 6 and 7, respectively. Reaction 4 and 5 with ethylchloroacelate gave the corresponding alkylated products 10 and 11 Better yields and much less time were the characteristic features of using the microwave heating over the conventional one. The structure of the prepared compounds was confirmed by H-1-NMR, 2D-NMR and mass spectra.