2,3,5-tri-O-benzyl-β-D-ribofuranosyl azide | 121682-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzyl-β-D-ribofuranosyl azide
• 英文别名: (2R,3R,4R,5R)-2-azido-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
• CAS: 121682-60-8
• 化学式: C₂₆H₂₇N₃O₄
• 分子量: 445.518
• InChiKey: QTEIWUHUEFZABZ-VEYUFSJPSA-N

物化性质

• 溶解度：
  二氯甲烷；氯仿；甲醇；

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-β-D-ribofuranosyl azide 在 10 wt% Pd(OH)2 on carbon 、 copper(I) thiocyanate 、 氢气 、 caesium carbonate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 20.0~70.0 ℃ 、405.33 kPa 条件下， 反应 46.0h， 生成 1-(β-D-ribofuranosyl)-4H-benzopyrano[3,4-d]-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of novel N-glycoside derivatives via CuSCN-catalyzed reactions and their SGLT2 inhibition activities

  摘要：

  A convenient approach to the synthesis of novel triazole-N-glycoside derivatives was developed via CuSCN-catalyzed click reaction and Ullmann-type coupling reaction for the first time. The SGLT2 inhibitory activities of these synthetic N-glycosides were evaluated, and some compounds showed moderate SGLT2 inhibition activities at 100 nM. The results could benefit the discovery of new SGLT2 inhibitors for the treatment of diabetes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.108
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苄氧基-1-beta-D-呋喃核糖 在 scandium(III) perchlorate 叠氮基三甲基硅烷 作用下， 以 乙醚 为溶剂， 反应 4.5h， 生成 2,3,5-tri-O-benzyl-β-D-ribofuranosyl azide 、 2,3,5-tri-O-benzyl-α-D-ribofuranosyl azide
  参考文献：
  名称：

  高氯酸（（III）（Sc（ClO 4）3）。α-C-和N-糖基化反应中的新型催化剂

  摘要：

  在催化量的高氯酸（（III）（Sc（ClO 4）3）存在下，1-O-乙酰基-2,3,5-三-O-苄基-β-D-呋喃呋喃糖与三甲基甲硅烷基化的亲核试剂反应生成以高收率和良好的选择性得到相应的α-D-呋喃核糖苷。反应完成后可以回收催化剂，并可以重复使用。

  DOI：

  10.1016/s0040-4039(00)76896-1

文献信息

• Bogusiak, Polish Journal of Chemistry, 2000, vol. 74, # 4, p. 503 - 507
  作者：Bogusiak

  DOI：——

  日期：——
• Inhibition of Carbonic Anhydrases with Glycosyltriazole Benzene Sulfonamides
  作者：Brendan L. Wilkinson、Alessio Innocenti、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm701426t

  日期：2008.3.1

  library of glycoconjugate benzene sulfonamides have been synthesized and investigated for their ability to inhibit the enzymatic activity of physiologically relevant human carbonic anhydrase (hCA) isozymes: hCA I, II, and tumor-associated IX. Our synthetic strategy directly links the known CA pharmacophore (ArSO2NH2) to a sugar "tail" moiety through a rigid 1,2,3-triazole linker unit using the Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction or "click chemistry". Many of the glycoconjugates were potent CA inhibitors and exhibited some isozyme selectivity. In particular, the methyl-D-glucuronate triazoles 6 and 14 were potent inhibitors of hCA IX (K(i)s 9.9 and 8.4 nM, respectively) with selectivity also favoring this isozyme. Other exceptional compounds included the deprotected beta-D-ribofuranosyl triazole 15 and alpha-D-mannosyl triazole 17, which were potent and selective hCA II inhibitors (K-i 7.5 nM and K-i 2.3 nM, respectively). Collectively, the results confirm that modification of ring size, stereochemical configuration, and chain length in the sugar tail moiety of glycoconjugate CA inhibitors permits tunable potency and selectivity that may constitute an important avenue for the future development of efficacious and selective CA-based therapeutics.
• MUKAIYAMA, TERUAKI;SUDA, SHINJI, CHEM. LETT.,(1990) N, C. 1143-1146
  作者：MUKAIYAMA, TERUAKI、SUDA, SHINJI

  DOI：——

  日期：——
• Synthesis of novel N-glycoside derivatives via CuSCN-catalyzed reactions and their SGLT2 inhibition activities
  作者：Shao-Tao Bai、De-Cai Xiong、Youhong Niu、Yan-Fen Wu、Xin-Shan Ye

  DOI：10.1016/j.tet.2015.05.108

  日期：2015.7

  A convenient approach to the synthesis of novel triazole-N-glycoside derivatives was developed via CuSCN-catalyzed click reaction and Ullmann-type coupling reaction for the first time. The SGLT2 inhibitory activities of these synthetic N-glycosides were evaluated, and some compounds showed moderate SGLT2 inhibition activities at 100 nM. The results could benefit the discovery of new SGLT2 inhibitors for the treatment of diabetes. (C) 2015 Elsevier Ltd. All rights reserved.
• Scandium(III) perchlorate (Sc(ClO4)3). A novel catalyst in the α-C- and N-glycosylation reactions
  作者：Iwao Hachiya、Shu Kobayashi

  DOI：10.1016/s0040-4039(00)76896-1

  日期：1994.5

  In the presence of a catalytic amount of scandium(III) perchlorate (Sc(ClO4)3), 1-O-acetyl-2,3,5-tri-O-benzyl-β-D-ribofuranose reacted with trimethylsilylated nucleophiles to afford the corresponding α-D-ribofuranosides in high yields with good selectivities. The catalyst could be recovered after the reactions were completed and could be reused.

  在催化量的高氯酸（（III）（Sc（ClO 4）3）存在下，1-O-乙酰基-2,3,5-三-O-苄基-β-D-呋喃呋喃糖与三甲基甲硅烷基化的亲核试剂反应生成以高收率和良好的选择性得到相应的α-D-呋喃核糖苷。反应完成后可以回收催化剂，并可以重复使用。