22529-61-9Relevant articles and documents
A Glucose-Derived α-Hydroxy Aldehyde for the Petasis Reaction: Facile Access to Polyfunctional δ-Amino Acids
Lenci, Elena,Bellini Puglielli, Raffaele,Bucaletti, Elisabetta,Innocenti, Riccardo,Trabocchi, Andrea
, p. 4227 - 4234 (2020)
The multicomponent Petasis borono-Mannich reaction proceeds via an imine with the boronic acid acting as the nucleophile for the preparation of amines and their derivatives, including amino acids. In view of the expansion of the poorly-exploited carbohydr
Synthesis and Glycosylation Properties of C6-Silylated Ido- and Gluco-Pyranosyl Donors
álvarez-Martínez, Ignacio,Pedersen, Christian Marcus
, (2020/07/24)
Silyl groups are widely used as alcohol protecting groups and their study has provided insight on some very remarkable structure and reactivity features within carbohydrate chemistry. However, not much work has been put into the effect on the reactivity of silyl groups directly attached to the sugar carbon chain. In this work, we have developed a synthetic methodology to obtain both d-glucosyl and l-idosyl donors containing a dimethylphenylsilyl group directly attached to C6. Glycosylation and competition experiments with different glycosyl acceptors have shown that this group is completely stable under glycosylation conditions and enhances reactivity beyond what a benzyl group attached to the sugar oxygen would do. Finally, we found adequate conditions for the protodesilylation of Si-containing glycosides to yield the 6-deoxy sugar analog.
Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands
Mishra, Nidhi,Singh, Anoop S.,Agrahari, Anand K.,Singh, Sumit K.,Singh, Mala,Tiwari, Vinod K.
, p. 389 - 399 (2019/05/06)
Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.