Rapid and efficient synthesis of α(1–2)mannobiosides

Abstract

α(1,2)mannobiosides with different substituents at the reducing end have been synthesized by a common strategy using benzoyls as the permanent protecting groups and an acetyl as the orthogonal protecting group at position C2 of the glycosyl acceptor. The new synthetic strategy has been performed remarkably reducing the number of purification steps, the time of synthesis (less than 72 hours) and improving the overall yield at least three times with respect to the best procedure described in the literature at the moment. Additionally, this protecting group strategy is compatible with the presence of azido groups and the use of Cu catalyzed azide alkyne cycloaddition (CuAAC) also called "click chemistry" for conjugating the α(1-2)mannobiosides to different scaffolds for the preparation of mannosyl multivalent systems.

Fluorescence Quenching‐based Assay for Measuring Golgi endo‐α‐Mannosidase

“…Removal of the tert‐butyl dimethylsilyl (TBS) protecting group and subsequent selective removal of the pivaloyl group at the non‐reducing end of the mannose residue gave compound 11 . The liberated hydroxyl groups of compound 11 were selectively acetylated via the orthoester derivative to give the C2 acetylated acceptor 12 in 61 % yield . The glucosyl donor 13 was synthesized in 4 % yield in 2 steps from a benzylidene glucose derivative (Scheme S1).…”

Applications of alkyl orthoesters as valuable substrates in organic transformations, focusing on reaction media

“…Several orthoesters were applied in various domains as dehydrating agents, [5][6][7][8][9][10][11][12][13][14][15][16][17][18] alkylating agents, [19][20][21][22][23][24] dialkoxymethylation agents, 25 esterication agents, 26 methoxy sources, 27 additives, [28][29][30] solvents, [31][32][33] and protecting groups. [34][35][36] This functional group is also necessary for some conversions such as the Johnson-Claisen rearrangement. 37 Fig.…”

Glycosylated Cell‐Penetrating Peptides (GCPPs)

“…[45][46][47][48][49] Theses trategies have deliverede xcellent peptides and relateda naloguesw ith applications in gene delivery, liposomef unctionalization, nanoparticle decoration, and therapeutic protein delivery. [43,[64][65][66][67][68][69][70][71] This strategy is aimed at targeting cellular membrane receptors and accumulatingg lycan-tagged ensembles at ap articular tissue. [59][60][61][62] For instance, the cationic charactero fC PPs, which is required form embrane anchoring and translocation, constitutes an important drawback because highly cationic molecules tend to stick nonspecifically in living tissues.…”