Stereoselective synthesis of 2-deoxy-β-C-aryl/alkyl glycosides using Prins cyclization: Application in the synthesis of C-disaccharides and differently protected C-aryl glycosides

2018 ◽  
Vol 468 ◽  
pp. 64-68 ◽  
Author(s):  
Sateesh Dubbu ◽  
Ande Chennaiah ◽  
Ashish Kumar Verma ◽  
Yashwant D. Vankar
Keyword(s):  
Stereoselective Synthesis ◽  
Prins Cyclization ◽  
Alkyl Glycosides ◽  
Aryl Glycosides

Highly regioselective and stereoselective synthesis of C-Aryl glycosides via Nickel-catalyzed ortho-C-H glycosylation of 8-aminoquinoline benzamides

2021 ◽  
Author(s):  
Wei-Yu Shi ◽  
Ya-Nan Ding ◽  
Nian Zheng ◽  
Xue-Ya Gou ◽  
Zhe Zhang ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Cost Effective ◽  
Drug Candidates ◽  
Aryl Glycosides ◽  
Glycosylation Reaction

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzed ortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows...

scholarly journals The Silylalkyne-Prins Cyclization: Stereoselective Synthesis of Tetra- and Pentasubstituted Halodihydropyrans.

ChemInform ◽  
2006 ◽  
Vol 37 (34) ◽  
Author(s):  
Pedro O. Miranda ◽  
Miguel A. Ramirez ◽  
Victor S. Martin ◽  
Juan I. Padron
Keyword(s):  
Stereoselective Synthesis ◽  
Prins Cyclization

Regio- and Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides via Palladium Catalyzed Decarboxylative Reactions

2011 ◽  
Vol 13 (17) ◽  
pp. 4608-4611 ◽  
Author(s):  
Shaohua Xiang ◽  
Shuting Cai ◽  
Jing Zeng ◽  
Xue-Wei Liu
Keyword(s):  
Stereoselective Synthesis ◽  
Palladium Catalyzed ◽  
Aryl Glycosides

Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D

2014 ◽  
Vol 12 (36) ◽  
pp. 7026-7035 ◽  
Author(s):  
Anil K. Saikia ◽  
Kiran Indukuri ◽  
Jagadish Das
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
Diastereoselective Synthesis ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Acyliminium Ions

A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.

A Metal-free and β-Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides: Synthesis of 5-aza analogues of Aquayamycin

Synlett ◽  
2021 ◽  
Author(s):  
Yuling Mei ◽  
nan jiang ◽  
Yu Yang ◽  
Wan Zhang ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Metal Free ◽  
Wide Range ◽  
One Step ◽  
Aryl Glycosides ◽  
Aryl Glycoside

A convenient protocol for β-stereoselective synthesis of 2-deoxy-C-aryl glycosides has been developed. This reaction takes place in one step by using I2/Et3SiH to activate glycosyl acetate to generate glycosyl iodide intermediate in situ, which was captured by naphthol followed by Fries-like O- → C-glycoside rearrangement to selectively afford β-C-aryl glycoside. The approach is applicable to a wide range of naphthol modules, and its utility was demonstrated in the synthesis of 5-aza analogues of Aquayamycin.

Tandem Prins Cyclization for the Stereoselective Synthesis of the 4,5-Diaryl-hexahydropyrano[3,4-c]chromene Skeleton of Calyxins I and J

2015 ◽  
Vol 2015 (14) ◽  
pp. 3103-3108 ◽  
Author(s):  
Basi V. Subba Reddy ◽  
Mittapalli Ramana Reddy ◽  
Sama Gopal Reddy ◽  
Balasubramanyan Sridhar ◽  
Singarapu Kiran Kumar
Keyword(s):  
Stereoselective Synthesis ◽  
Prins Cyclization

ChemInform Abstract: Tandem Prins Cyclization for the Stereoselective Synthesis of Bridged Benzopyran Derivatives.

ChemInform ◽  
2016 ◽  
Vol 47 (51) ◽  
Author(s):  
Basi V. Subba Reddy ◽  
Nikhil Srivastava ◽  
Zubeda Begum ◽  
Jerripothula K. Lakshmi ◽  
Balasubramanian Sridhar
Keyword(s):  
Stereoselective Synthesis ◽  
Prins Cyclization

ChemInform Abstract: Completely OH-Selective FeCl3-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans.

ChemInform ◽  
2013 ◽  
Vol 44 (16) ◽  
pp. no-no
Author(s):  
Ke Zheng ◽  
Xiaohua Liu ◽  
Song Qin ◽  
Mingsheng Xie ◽  
Lili Lin ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Prins Cyclization

ChemInform Abstract: Domino Prins Cyclization of Enynols: Stereoselective Synthesis of Bicyclic Vinyl Fluorides.

ChemInform ◽  
2015 ◽  
Vol 46 (51) ◽  
pp. no-no
Author(s):  
Anipireddy Venkateswarlu ◽  
Marumudi. Kanakaraju ◽  
Ajit C. Kunwar ◽  
Yellala V. Rami Reddy ◽  
Basi V. S. Reddy
Keyword(s):  
Stereoselective Synthesis ◽  
Prins Cyclization ◽  
Vinyl Fluorides
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