Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization

Main Article Content

Laxminarayan Sahoo
Anadi Singhamahapatra
Satyanarayan Sahoo

Abstract

A series of novel 1,3-difunctionalized glycoconjugates were synthe­sized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 function­aliz­ation of sugar molecules was achieved by chemical functionalization of iso­pro­pylidene or oxazoline protected sugar derivatives. The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation. The oxazoline protected D-GlcNAc derivative gave either pyranose or fura­nose derivatives on glycosidation depending on the amount of Lewis acid used. The diversely functionalized glycoconjugates with azide or alkyne groups are potentially useful for the synthesis of multifunctionalized complex glycocon­jugates via click reactions.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Article Details

How to Cite
[1]
L. Sahoo, A. Singhamahapatra, and S. Sahoo, “Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization”, J. Serb. Chem. Soc., vol. 83, no. 5, pp. 539–548, Jun. 2018.
Section
Organic Chemistry
Author Biographies

Laxminarayan Sahoo, District Forensic Science Laboratory, Puri 752002, Odisha

Chemistry

Scientific Officer

Anadi Singhamahapatra, Saraswati Degree Vidya Mandir, Neelakantha Nagar, Berhampur760002, Odisha

Department of Chemistry

Lecturer

Satyanarayan Sahoo, P. G. Department of Chemistry, Berhampur University, Berhampur 760007, Odisha

P. G. Departmanr of Chemistry

Assistant Professor

References

S. L. Schreiber,M. D. Burke, Angew. Chem. Int. Ed. 43 (2004) 46

S. L. Schreiber, Science 287 (2000) 1964

R. J. Spandl, A. Benderb, D. R. Spring, Org. Biomol. Chem. 6 (2008) 1149

C. Manna, T. Pathak, Eur. J. Org. Chem. 27 (2013) 6084

A. Cordeiro, E. Quesada, M. C. Bonache, S. Velázquez, M. J. Camarasa, A. San-Félix, J. Org. Chem. 71 (2006) 7224

S. Kashyap, S. Hotha, Tetrahedron Lett. 47 (2006) 2021

A. Varki, Glycobiology 27 (2017) 3

V. Wittmann, R. J. Pictere, Chem. Soc. Rev. 42 (2013) 4492

B. G. Davis, J. Chem. Soc. Perkin Trans. 1 (1999) 3215

P. M. Dandy, S. G. Withers, ACS Chem. Biol. 11 (2016) 1784

R. Mahrwald, Chem. Commun. 51 (2015) 13868

K. Villadsen, M. C. Martos-Maldonado, K. J. Jensen, M. B. Thygesen, ChemBioChem 18 (2017) 574

R. Sangwan, P. K. Mandal, RSC Adv. 7 (2017) 26256

B. K. Sharpless, Angew. Chem. Int. Ed. 41 (2002) 2596

B. H. M. Kuijpers, S. Groothuys, A. R. Keereweer, P. J. L. M. Qauedflieg, R. H. Blaauw, F. L. van Delft, F. P. J. T. Rutjes, Org. Lett. 6 (2004) 3123

L. Sahoo, A. Singhamahapatra, K. Kumar, D. Loganathan, Carbohydr. Res. 381 (2013) 51

A. Singhamahapatra, L. Sahoo, D. Loganathan, J. Org. Chem. 78 (2013) 10329

L. Sahoo, A. Singhamahapatra, K. J. V. Paul, D. Loganathan, Tetrahedron Lett. 54 (2013) 5361

L. Sahoo, A. Singhamahapatra, D. Loganathan, Org. Biomol. Chem. 12 (2014) 2615

R. S. Nandurdikar, A. V. Subrahmanyam, K. P. Kaliappan, Eur. J. Org. Chem. 14 (2010) 2788

H. Zhang, A. Padwa, Org. Lett. 8 (2006) 247

H. Tanaka, H. Tago, Y. Adachi, N. Ohno, T. Takahasi, Tetrahedron Lett. 53 (2012) 4104

T. L. Lowary, Y. Cai, F. Skogman, C. Liu, Carbohydr. Res. 342 (2007) 2818

S. A. Allman, H. H. Jensen, B. Vijayakrishnan, J. A. Garnett, E. Leon, Y. Liu, D. C. Anthony, N. R. Sibson, T. Feizi, S. Matthews, B. G. Davis, ChemBioChem 10 (2009) 2522

Y. Cai, C. Ling, D. R. Bundle, Org. Lett. 7 (2005) 4021

Y. Cai, C. Ling, D. R. Bundle, J. Org. Chem. 74 (2009) 580

Z. Zhan, F. Ren, Y. Zhao, Carbohydr. Res. 345 (2010) 315

A. Singhamahapatra, L. Sahoo, S. Kundu, D. Loganathan, Trends Carb. Res. 5 (2013) 39.

Most read articles by the same author(s)