Recent advances in direct synthesis of 2-deoxy glycosides and thioglycosides

S Meng, X Li, J Zhu - Tetrahedron, 2021 - Elsevier
Deoxy sugars exist in numerous bioactive molecules and exert significant influences on their
physical, chemical, and biological properties. Due to the absence of directing group at C-2 …

Stereoselective Synthesis of Glycosides via Tsuji–Trost Type Glycosylation Using 3,4‐Carbonate Galactals

YL Kim, JH Kim - The Chemical Record, 2024 - Wiley Online Library
Pd‐catalyzed stereoselective glycosylations using unsaturated sugar derivatives, glycals,
have been successfully achieved in recent years. This review focuses on approaches to …

L‐Proline Derived Thioamide Small Organic Molecule for the α‐Stereoselective Synthesis of 2‐Deoxyglycosides

A Tiwari, A Khanam, A Kumar, M Lal… - Advanced Synthesis …, 2023 - Wiley Online Library
L‐Prolinethioamide catalyzes direct stereoselective glycosylation of glycal donors to access
2‐deoxyglycosides under moderate reaction conditions. This proposed glycosylation …

Bismuth-catalyzed stereoselective 2-deoxyglycosylation of disarmed/armed glycal donors

M Kumar, A Gurawa, N Kumar, S Kashyap - Organic Letters, 2022 - ACS Publications
Bi (OTf) 3 promoted direct and highly stereoselective glycosylation of “disarmed” and
“armed” glycals to synthesize 2-deoxyglycosides has been reported. The tunable and …

Influence of C-4 Axial/Equatorial Configuration and Neighboring Group/Remote Group Participation (NGP/RGP) Driven Conformational Evidence in Chemoselective …

N Kumar, A Gurawa, A Yadav, S Kashyap - Organic Letters, 2024 - ACS Publications
We herein reveal the possibility of the C-4 neighboring group/remote group participation
(NGP/RGP) facilitating the stabilization of the anomeric center via dioxolenium intermediates …

Development of α-Selective Glycosylation with l-Oleandral and Its Application to the Total Synthesis of Oleandrin

N Carney, N Perry, J Garabedian, P Nagorny - Organic letters, 2023 - ACS Publications
This letter describes the development of an α-selective glycosylation using l-oleandrose, a 2-
deoxysugar that is frequently found in natural products, and its application to the total …

Metal nanoparticles incorporated within graphene-enzyme preparations for synergistic multiactive catalysts

N Losada-Garcia, EP Urriolabeitia… - ACS Applied Nano …, 2022 - ACS Publications
The development of catalytic systems with different chemo-and biocatalytic functionalities for
sustainable one-pot multistep transformations represents a big challenge in modern …

Reagent-controlled chemo/stereoselective glycosylation of ʟ-fucal to access rare deoxysugars

N Kumar, M Yadav, S Kashyap - Carbohydrate Research, 2024 - Elsevier
Dideoxy sugars constitute an important class of anticancer antibiotics natural products and
serve as essential medicinal tools for carbohydrate-based drug discovery and vaccine …

Ni‐Catalyzed Cross‐Coupling of 2‐Iodoglycals and 2‐Iodoribals with Grignard Reagents: A Route to 2‐C‐Glycosides and 2'‐C‐Nucleosides

P Polák, J Cossy - Chemistry–A European Journal, 2022 - Wiley Online Library
The synthesis of 2‐C‐glycals and 2‐C‐ribals was achieved in good yields using a nickel‐
catalyzed cross‐coupling between 2‐iodoglycals and 2‐iodoribal respectively and Grignard …

Catalytic stereoselective synthesis of 2-deoxy α-glycosides using glycosyl ortho-[1-(p-MeOPhenyl) Vinyl] Benzoate (PMPVB) donors

S Halder, RB Addanki, BK Sarmah… - Organic & Biomolecular …, 2022 - pubs.rsc.org
2-Deoxy glycosyl ortho-[1-(p-MeOPhenyl) Vinyl] Benzoates (PMPVB) have been presented
as stable, reactive glycosyl donors for the synthesis of 2-deoxy α-glycosides. The donors …