Synthesis of l-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors?
Organic & Biomolecular Chemistry Pub Date: 2014-08-08 DOI: 10.1039/C4OB01319K
Abstract
Herein we describe the synthesis of a series of novel fused bicyclic 1,2,3-triazoles from commercially available, natural deoxy sugar, L-rhamnose. The key reactions involved are (i) Zn(OTf)2 catalyzed enantioselective alkynylation of L-rhamnose derived azidoaldehyde and (ii) deprotection of the acid sensitive 1,2-isopropylidene group followed by in situ intramolecular click-cycloaddition of azidoalkynols. Some compounds exhibit excellent sodium-glucose transporter (SGLT1 and SGLT2) inhibition activity.
Recommended Literature
- [1] An anti-leakage liquid metal thermal interface material Kaiyuan Huang,Wangkang Qiu,Meilian Ou,Xiaorui Liu,Zenan Liao,Sheng ChuRSC Adv., 2020,10, 18824-18829 10.1039/D0RA02351E
- [2] An integrated digital microfluidic chip for multiplexed proteomic sample preparation and analysis by MALDI-MS? Hyejin Moon,Aaron R. Wheeler,Robin L. Garrell,Chang-Jin “CJ” KimLab Chip, 2006,6, 1213-1219 10.1039/B601954D
- [3] An artificial CO-releasing metalloprotein built by histidine-selective metallation? Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?oChem. Commun., 2015,51, 3993-3996 10.1039/C4CC10204E
- [4] An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis? Supaporn Sawadjoon,Joseph S. M. SamecOrg. Biomol. Chem., 2011,9, 2548-2554 10.1039/C0OB00383B
- [5] An aptasensor for the detection of ampicillin in milk using a personal glucose meter Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu ZhangAnal. Methods, 2020,12, 3376-3381 10.1039/D0AY00256A
- [6] Acetyl protected thiol methacrylic polymers as effective ligands to keep quantum dots in luminescent standby mode? Marta Liras,Isabel Quijada-Garrido,Marta Palacios-Cuesta,Sonia Mu?oz-Durieux,Olga GarcíaPolym. Chem., 2014,5, 433-442 10.1039/C3PY00987D
- [7] An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes? Bo Cao,Yin WeiChem. Commun., 2018,54, 2870-2873 10.1039/C8CC00180D
- [8] An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction? Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin JinJ. Mater. Chem. C, 2020,8, 192-200 10.1039/C9TC05297F
- [9] Aggregation dynamics, structure, and mechanical properties of bigels L. Di Michele,D. Fiocco,F. Varrato,E. Eiser,G. FoffiSoft Matter, 2014,10, 3633-3648 10.1039/C3SM52558A
- [10] An artificial photosynthetic system for photoaccumulation of two electrons on a fused dipyridophenazine (dppz)–pyridoquinolinone ligand? Philipp Traber,Stephan Kupfer,Stefanie Gr?fe,Isabelle Baussanne,Martine Demeunynck,Jean-Marie Mouesca,Serge Gambarelli,Vincent Artero,Murielle Chavarot-KerlidouChem. Sci., 2018,9, 4152-4159 10.1039/C7SC04348A
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)