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Organocatalysis and Carbohydrate chemistry

laboratory

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2024

Pradhan, P.; Moktan, S.; Halder, Biswas, A.; Das, A.; Lenka, R.; Bhattacharya, K.; Kancharla, P. K.* “Triple Role of Proton Sponge (DMAN) in the Palladium-Catalyzed Direct Stereoselective Synthesis of C-Aryl Glycosides from Glycals”Org. Lett. 2024, ASAP.

Addanki, R. B.; Moktan, S.; Halder, S. H.; Sharma, M.; Sarmah, B. K.; Bhattacharya, K.; Kancharla, P. K.* “Exploiting the Strained Ion-Pair Interactions of Sterically Hindered Pyridinium Salts Toward SN2 Glycosylation of Glycosyl Trichloroacetimidates” J. Org. Chem. 2024, ASAP.

2023

Moktan, S.; Rotta, M.K.V.; Halder, S. H.; Pradhan, P.; Kancharla, P. K.* "Synthesis of Chiral Functional Polyhydroxylated Arenes via Mukaiyama Aldol Reaction from Perlin Aldehydes" Carbohydrate Research. 2023, ASAP. Link. Invited article!!

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Moktan, S.; Rotta, M.K.V.; Halder, S. H.; Pradhan, P.; Kancharla, P. K.* "Ortho-[1-(p-MeOPhenyl) Vinyl] Benzoate (PMPVB) as a Recyclable auxiliary for C-O and C-S bond formation Reactions Under Bronsted acid Catalysis" Org. & Biomol. Chem. 2023,21, 5929-5934. Link.

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Halder, S. H.; Addanki, R. B.; Kancharla, P. K.* “Regio- and Stereoselective C-Glycosylation of Indoles Using o-[1-(p-MeO-Phenyl)vinyl]benzoates (PMPVB) as Glycosyl Donors under Brønsted Acid Catalysis” J. Org. Chem. 2023, 88, 3, 1844-1854, ASAP.

Mukherji, A.; Mahendra, K. V. Rotta; Kancharla, P. K.* “Influence of Various Silyl Protecting Groups on Stereoselective 2-Deoxyrhamnosylation” J. Org. Chem. 2023, 88, 245-260.

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2022

Mukherji, A.; Kancharla, P. K.* “Cl-…H-N Interactions Assisted Addition of Sulfonamides to Enol Ethers: Synthesis of 2-deoxy and 2,6-Dideoxy Sulfonamido Glycosides” Synlett 2022, Just Accepted. Invited Article! for a special issue on "Chemical Synthesis and Catalysis in India" Link.

Halder, S. H.; Addanki, R. B.; Moktan, S.; Kancharla, P. K.* “Glycosyl Ortho-[1-(p-MeOPhenyl)Vinyl]Benzoates (PMPVB) as Easily Accessible, Stable, and Reactive Glycosyl Donors for O-, S- and C-glycosylations Under Brønsted Acid Catalysis” J. Org. Chem. 2022, ASAP Link.

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Addanki, R. B.; Halder, S. H.; Kancharla, P. K.* “TfO–···H–O–H Interaction-Assisted Generation of a Silicon Cation from Allylsilanes: Access to Phenylallyl Ferrier Glycosides from Glycals” Org. Lett. 2022, 24, 7, 1465-1470 Link.

Halder, S. H.; Addanki, R. B.; Kancharla, P. K.* “Catalytic stereoselective synthesis of 2-deoxy α-glycosides using glycosyl ortho-[1-(p-MeOPhenyl)Vinyl]Benzoate (PMPVB) donors” Org. & Biomol. Chem. 2022, ASAP.. Link.

2021

Mukherji, A.; Addanki, R. B.; Halder, S. H.; Kancharla, P. K.* “Sterically Strained Brønsted Pair Catalysis by Bulky Pyridinium Salts: Direct Stereoselective Synthesis of 2-Deoxy and 2,6-Dideoxy-β-thioglycosides from Glycals” J. Org. Chem. 2021, 86, 17226-17243. Link.

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Priyanka Adhikari, Dipanjan Bhattacharyya, Sekhar Nandi, Pavan K. Kancharla and Animesh Das* “Reductive Alkylation of Quinolines to N-Alkyl Tetrahydroquinolines Catalyzed by Arylboronic Acid” Org. Lett. 2021, 23, 2437-2442. Link.

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Ghosh, T.; Mukherji, A.; Kancharla, P. K.* “Influence of Anion-Binding Schreiner’s Thiourea on DMAP Salts: Synergistic Catalysis toward the Stereoselective Dehydrative Glycosylation from 2-Deoxyhemiacetals” J. Org. Chem. 2021, 86, 1253-1261. Link.

2020

Mukherji, A.; Kancharla, P. K.* “C−H···Anion Interactions Assisted Addition of Water to Glycals by Sterically Hindered 2,4,6-Tri-tert-butylpyridinium Hydrochloride” Org. Lett. 2020, 22, 2191–2195. Link.

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Halder, S.; Addanki, R. B.; Kancharla, P. K.* "Three Step Synthesis of L-Altrose from D-glucal derived Perlin Aldehyde" JICS, 2020, 97, 2, 243-250. Special Issue on Synthetic Carbohydrate Chemistry. Invited Article!! Link.

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2019

Ghosh, T.; Mukherji, A.; Kancharla, P. K.* “Open‐Close Strategy toward the Organocatalytic Generation of 2‐Deoxyribosyl Oxocarbenium Ions: Pyrrolidine‐Salt‐Catalyzed Synthesis of 2‐Deoxyribofuranosides” Eur. J. Org. Chem. 2019, 7488–7498. Link.

Pawar, N. J.; Lei, W.; Higo, T.; Bhattacharya, C.; Kancharla, P. K.; Zhang, F.; Baryal, K.; Huo, C-X.; Liu, J.; Linhardt, R. J.; Huang, X.; Hsieh-Wilson, L. C.; “Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly” Angew Chem. Int. Ed. 2019, 58, 18577-18583. Link.

Ghosh, T.; Mukherji, A.; Kancharla, P. K.* “Sterically Hindered 2,4,6-Tri-tert-butylpyridinium Salts as Single Hydrogen Bond Donors for Highly Stereoselective Glycosylation Reactions of Glycals” Org. Lett. 2019, 21, 3490–3495. Link.

2018

Ghosh, T.; Mukherji, A.; Srivastava, H. K.; Kancharla, P. K.* “Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha- selective dehydrative glycosylation” Org. Biomol. Chem. 2018, 16, 2870–2875. Link.

Before 2015

Kancharla, P. K.; Takayuki Kato; David Crich, “Probing the Influence of Protecting Groups on the Anomeric Equilibrium in Sialic Acid Glycosides with the Persistent Radical Effect” J. Am. Chem. Soc., 2014, 136 (14), 5472-5480.

Pavan K. Kancharla; David Crich, "Influence of Side Chain Conformation and Configuration on Glycosyl Donor Reactivity and Selectivity as Illustrated by Sialic Acid Donors Epimeric at the 7-Position" J. Am. Chem. Soc., 2013, 135 (50), 18999-19007.

Rashmi Roy; Pavan K. Kancharla; Y. Suman Reddy; Anita Brar; Y. D. Vankar, "Synthesis of isofagomine and some new azasugars as glycosidase inhibitors from D-mannitol derived nitroolefins" Tetrahedron: Asymmetry 2013, 24, 1502-1513.

Suresh Dharuman; Preeti Gupta; Pavan K. Kancharla; Y. D. Vankar, "Synthesis of 2-Nitroglycals from Glycals Using the Tetrabutyl ammonium Nitrate-Trifluoroacetic Anhydride-Triethylamine Reagent System and Base-Catalyzed Ferrier Rearrangement of Acetylated 2-Nitroglycals" J. Org. Chem. 2013, 78(17), 8442-8450.

Pavan K. Kancharla; Chandrasekhar Navuluri; David Crich, "Dissecting the Influence of Oxazolidinones and Cyclic Carbonate Groups in Sialic Acid Chemistry" Angew. Chem. Int. Ed. 2012, 51, 11105-11109.

Y. Suman Reddy; Pavan K. Kancharla; Rashmi Roy; Y. D. Vankar, "Aza-Claisen rearrangement of 2-C-hydroxymethyl glycals as a versatile strategy towards isofagomine and related biologically important azasugars" Org. & Biomol. Chem. 2012, 10, 2760-2773.

Pavan K. Kancharla; Y. Suman Reddy; Suresh Dharuman; Y. D. Vankar, "A New Reagent System for the preparation of Nitro Olefins and Nitro Acetamides" J. Org. Chem. 2011, 76(14), 5832-5837.

Pavan K. Kancharla; Y. D. Vankar "Chemistry of 2-nitroglycals: A One-Pot Three Component Stereoselective Approach Towards 2-C-Branched O-Galatcosides" J. Org Chem. 2010, 75, 8457-864.

Pavan K. Kancharla; Venkata Ramana Doddi; Hariprasad Kokatla; Y. D. Vankar, "A concise route to (?)-shikimic acid and (?)-5-epi-shikimic acid, and their enantiomers via Barbier reaction and ring-closing metathesis" Tet. Lett. 2009, 50, 6951-6954.

Hariprasad Kokatla; Rima Lahiri; Pavan K. Kancharla; Venkata Ramana Doddi; Y. D. Vankar, "Synthesis of (?) Deoxoprosophylline, (+)-2-epi-Deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-Hydroxy pipecolic Acids from D-Glycals" J. Org. Chem. 2010, 75, 4608-4611.

Venkata Ramana Doddi; Pavan K. Kancharla; Y. Suman Reddy; Y. D. Vankar; "Synthesis of fused pyran-carbahexopyranoses as glycosidase inhibitors" Carb. Res. 2009, 344, 606-612.

Book Chapters

"2H-2-hydroxy-1,3,2-benzodithiazole 1,1,3,3-tetraoxide." Electronic Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, John Wiley & Sons. Ltd. 2013, Pavan K. Kancharla

"(2S)-N-(2,3,4,5,6-pentafluorophenyl)-2-pyrrolidinecarboxamide." Electronic Encyclo-pedia of Reagents for Organic Synthesis, ed. L. A. Paquette, John Wiley & Sons. Ltd. 2013, Pavan K. Kancharla.

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