3,5-dichloro-1-(2,3,4-tri-O-pivaloyl-β-D-xylopyranosyl)-1,2,4-triazole | 886984-84-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-dichloro-1-(2,3,4-tri-O-pivaloyl-β-D-xylopyranosyl)-1,2,4-triazole
• 英文别名: [(3R,4S,5R,6R)-6-(3,5-dichloro-1,2,4-triazol-1-yl)-4,5-bis(2,2-dimethylpropanoyloxy)oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 886984-84-5
• 化学式: C₂₂H₃₃Cl₂N₃O₇
• 分子量: 522.426
• InChiKey: CEVPKIWOVFRCDU-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,5-dichloro-1-(2,3,4-tri-O-pivaloyl-β-D-xylopyranosyl)-1,2,4-triazole 、 4-乙烯基苯硼酸 在 palladium diacetate potassium phosphate 、 [(adamantyl)2PHBu]⁽¹⁺⁾*I^(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到3-chloro-5-(4-vinylphenyl)-1-(2,3,4-tri-O-pivaloyl-β-D-xylopyranosyl)-1,2,4-triazole
  参考文献：
  名称：

  First cross-coupling reactions on halogenated 1H-1,2,4-triazole nucleosides

  摘要：

  The halogenated 1H-1,2,4-triazole glycosides 6-10 were synthesized by BF3-activated glycosylation of 3(5)-chloro-1,2,4-triazole (2), 3,5-dichloro-1,2,4-triazole (3), 3,5-dibromo-1,2,4-triazole (4), and 3(5)-bromo-5(3)-chloro-1,2,4-triazole (5) with 1,2,3,4-tetra-O-pivaloyl-beta-D-xylopyranose (1). The beta-anomeric major products 3-chloro-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (6 beta), 3,5-dichloro-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (7 beta), and 3,5-dibromo-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)1,2,4-triazole (8 beta) were used as starting materials for transition metal catalyzed C-C-coupling reactions. Arylations of the triazole ring of 7 beta, and 8 beta were successful in 5-position with phenylboronic acid, 4-vinylphenylboronic acid, and 4-methoxyphenylboronic acid, respectively, under Suzuki cross-coupling conditions (products 11-17). Moreover, a Cu-catalyzed perfluoroalkylation of 8 beta is reported with 1-iodo-perfluorohexane yielding 3-perfluorohexyl-1-(2,3,4-tri-0-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (18). Compound 18 was depivaloylated to the trihydroxy derivative 19. The copper-mediated reaction of 8 beta with Rupert's reagent gave the bis(3-bromo-1-(2,3,4-tri-0-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazol-5-yl) (20). beta 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.053
• 作为产物：
  描述：

  3,5-二氯-1H-1,2,4-噻唑 、 1,2,3,4-Tetra-O-pivaloyl-β-D-xylopyranose 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以69%的产率得到3,5-dichloro-1-(2,3,4-tri-O-pivaloyl-β-D-xylopyranosyl)-1,2,4-triazole
  参考文献：
  名称：

  First cross-coupling reactions on halogenated 1H-1,2,4-triazole nucleosides

  摘要：

  The halogenated 1H-1,2,4-triazole glycosides 6-10 were synthesized by BF3-activated glycosylation of 3(5)-chloro-1,2,4-triazole (2), 3,5-dichloro-1,2,4-triazole (3), 3,5-dibromo-1,2,4-triazole (4), and 3(5)-bromo-5(3)-chloro-1,2,4-triazole (5) with 1,2,3,4-tetra-O-pivaloyl-beta-D-xylopyranose (1). The beta-anomeric major products 3-chloro-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (6 beta), 3,5-dichloro-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (7 beta), and 3,5-dibromo-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)1,2,4-triazole (8 beta) were used as starting materials for transition metal catalyzed C-C-coupling reactions. Arylations of the triazole ring of 7 beta, and 8 beta were successful in 5-position with phenylboronic acid, 4-vinylphenylboronic acid, and 4-methoxyphenylboronic acid, respectively, under Suzuki cross-coupling conditions (products 11-17). Moreover, a Cu-catalyzed perfluoroalkylation of 8 beta is reported with 1-iodo-perfluorohexane yielding 3-perfluorohexyl-1-(2,3,4-tri-0-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (18). Compound 18 was depivaloylated to the trihydroxy derivative 19. The copper-mediated reaction of 8 beta with Rupert's reagent gave the bis(3-bromo-1-(2,3,4-tri-0-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazol-5-yl) (20). beta 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.053

文献信息

• First cross-coupling reactions on halogenated 1H-1,2,4-triazole nucleosides
  作者：Susanne Wille、Martin Hein、Ralf Miethchen

  DOI：10.1016/j.tet.2006.01.053

  日期：2006.4

  The halogenated 1H-1,2,4-triazole glycosides 6-10 were synthesized by BF3-activated glycosylation of 3(5)-chloro-1,2,4-triazole (2), 3,5-dichloro-1,2,4-triazole (3), 3,5-dibromo-1,2,4-triazole (4), and 3(5)-bromo-5(3)-chloro-1,2,4-triazole (5) with 1,2,3,4-tetra-O-pivaloyl-beta-D-xylopyranose (1). The beta-anomeric major products 3-chloro-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (6 beta), 3,5-dichloro-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (7 beta), and 3,5-dibromo-1-(2,3,4-tri-O-pivaloyl-beta-D-xylopyranosyl)1,2,4-triazole (8 beta) were used as starting materials for transition metal catalyzed C-C-coupling reactions. Arylations of the triazole ring of 7 beta, and 8 beta were successful in 5-position with phenylboronic acid, 4-vinylphenylboronic acid, and 4-methoxyphenylboronic acid, respectively, under Suzuki cross-coupling conditions (products 11-17). Moreover, a Cu-catalyzed perfluoroalkylation of 8 beta is reported with 1-iodo-perfluorohexane yielding 3-perfluorohexyl-1-(2,3,4-tri-0-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazole (18). Compound 18 was depivaloylated to the trihydroxy derivative 19. The copper-mediated reaction of 8 beta with Rupert's reagent gave the bis(3-bromo-1-(2,3,4-tri-0-pivaloyl-beta-D-xylopyranosyl)-1,2,4-triazol-5-yl) (20). beta 2006 Elsevier Ltd. All rights reserved.