3-(1,2,3,4,5-penta-O-acetyl-D-gluco-pentitol-1-yl)-1H-1,2,4-triazole | 335065-53-7

• 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: 3-(1,2,3,4,5-penta-O-acetyl-D-gluco-pentitol-1-yl)-1H-1,2,4-triazole
• 英文别名: 3-(1,2,3,4,5-penta-O-acetyl-D-gluco-pentitol-1-yl)-4H-1,2,4-triazole；[(2R,3R,4R,5S)-2,3,4,5-tetraacetyloxy-5-(1H-1,2,4-triazol-5-yl)pentyl] acetate
• CAS: 335065-53-7
• 化学式: C₁₇H₂₃N₃O₁₀
• 分子量: 429.384
• InChiKey: AIMNDDLFLDQNNO-LVQVYYBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-(1,2,3,4,5-penta-O-acetyl-D-gluco-pentitol-1-yl)-1H-1,2,4-triazole 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以70%的产率得到3-(D-gluco-pentitol-1-yl)-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：

  乙酸酐 、 4-amino-3-(D-gluco-pentitol-1-yl)-5-mercapto-4H-1,2,4-triazole 在 磷酸 、 sodium nitrite 、 吡啶 作用下， 反应 0.03h， 以63%的产率得到3-(1,2,3,4,5-penta-O-acetyl-D-gluco-pentitol-1-yl)-1H-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

文献信息

• NOVEL SYNTHESIS OF<i>seco</i>TYPE OF ACYCLO<i>C</i>-NUCLEOSIDES OF 1,2,4-TRIAZOLE AND 1,2,4-TRIAZOLO[3,4-b][1,3,4]THIADIAZINE
  作者：El Sayed H. El Ashry、Laila F. Awad

  DOI：10.1081/ncn-100001440

  日期：2001.2.26

  -mercapto-1,2,4-triazole (12) with phenacylbromide (11) afforded the corresponding 3-(D-gluco-, D-galacto-pentitol-1-yl) and 3-(D-glycero-D-gulo-hexitol-1-yl)-6-phenyl-7H-1,2,4- triazolo[3,4-b][1,3,4] thiadiazines (15, 16, and 17). Acetylation of 15–17 gave the penta- and hexa-O-acetyl derivatives 18–20, respectively. The structures were confirmed by using 1H, 13C, and 2D NMR spectra, DQFCOSY, HMQC

  Seco C-核苷3-（1,2,3,4,5-penta-O-乙酰基-D-葡萄糖-和D-半乳糖-戊糖醇-1-基）-1H-1,2,4-三唑（在一锅中通过对4-氨基-3-（D-葡萄糖和D-半乳糖-戊糖醇-1-基）-5-巯基-1,2,4-三唑（ 1和2），分别在正磷酸中使用亚硝酸钠，然后进行乙酰化。1，2，和4-氨基-3-（D-甘油-D-果糖己糖醇-1-基）-5-巯基-1,2,4-三唑（12）与苯乙溴（11）的缩合反应相应的3-（D-葡萄糖基，D-半乳糖基戊糖醇-1-基）和3-（D-甘油-D-gulo-己糖醇-1-基）-6-苯基-7H-1,2,4- triazolo [3,4-b] [1,3,4]噻二嗪（15、16和17）。乙酰化15-17分别生成五-和六-O-乙酰基衍生物18-20。通过使用1H，13C和2D NMR光谱，DQFCOSY，HMQC和HMBC实验来确认结构。
• <i>SECO</i>C-NUCLEOSIDE ANALOGS OF THE 1,2,4-TRIAZOLE
  作者：El Sayed H. El Ashry、Laila F. Awad

  DOI：10.1081/ncn-100002455

  日期：2001.3.31

  The seco C-nucleosides 3-(1,2,3,4,5-penta-O-acetyl-D-gluco- and D-galacto-pentitol-1-yl)-1H-1,2,4-triazoles (6 and 7) were obtained in one pot by deamination and dethiolation of 4-amino-3-(D-gluco- and D-galacto-pentitol-1-yl)-5-mercapto-1,2,4-triazoles (1 and 2), respectively, using sodium nitrite in orthophosphoric acid and subsequent acetylation. The structures were confirmed by using 1H, 13C and

  Seco C-核苷3-（1,2,3,4,5-戊-O-乙酰基-D-葡萄糖-和D-半乳糖-戊醇-1-基）-1H-1,2,4-三唑（一锅中通过4-氨基-3-（D-葡萄糖和D-半乳糖戊糖醇-1-基）-5-巯基-1,2,4-三唑的脱氨基和脱硫反应获得6和7）和2）分别使用亚磷酸钠的正磷酸溶液和随后的乙酰化反应。通过使用1H，13C和2D NMR光谱，DQFCOSY，HMQC和HMBC实验来确认结构。从质子的邻偶耦合常数推导了有利的构象结构。