106567-65-1

Upstream product

• 106567-62-8 tert-Butyldimethylsilyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid 
• 99049-62-4 2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 182265-61-8 C₅₂H₅₉N₃O₁₁ 
• 182118-37-2 C₅₂H₅₉N₃O₁₁ 

Relevant academic research and scientific papers

A highly stereoselective construction of 1,2-trans-β-glycosidic linkages capitalizing on 2-azido-2-deoxy-D-glycosyl diphenyl phosphates as glycosyl donors

The scope of TMSOTf-promoted glycosidation of 2-azido-2-deoxyglycopyranosyl diphenyl phosphates is investigated. The 3,4,6-tri-O-benzyl-protected glucosyl and galactosyl donors and the 4,6-O-benzylidene-protected galactosyl donor each react with a range of acceptor alcohols in the presence of a stoichiometric amount of TMSOTf in propionitrile at -78°C to afford 1,2-trans-β-linked disaccharides in high yields with α:β ratios ranging from 9:91 to 1:>99, regardless of the anomeric composition of the donor used. The use of propionitrile as a solvent at -78°C has proven to be among the best choice for the highest levels of β-selectivity reported to date for this type of glycosidation. A plausible reaction mechanism, which features a large equilibrium preference for α-glycosyl-nitrilium ions over β-nitrilium ions, is proposed based on byproducts formed through their intermediacy and accounts for the observed excellent β-selectivities. Graphical Abstract.

Glycosyl Imidates, 25.- Muramic Acid as Glycosyl Donor and Glycosyl Acceptor

From the 3-O-unprotected 2-azido-2-deoxy-D-glucose derivatives 3 and 4 and trifluoromethanesulfonates of (S)-lactate as alkylating agents the muramic acid derivatives 8a-10a were obtained diastereospecifically and in high yields. (S)-2-Chloropropionates afforded mixtures of diastereoisomers in this reaction.The muramic acid derivatives 8a-10a were readily transformed into glycosyl donors and glycosyl acceptors.Deacetalation of compounds 8a and 10a and subsequent selective 6-O-silylation afforded the glycosyl acceptor 11; reaction with α-trichloroacetimidate 14 as glycosyl donor provided the β-connected disaccharide 15-β.Deprotection yielded the disaccharide 19, the basic unit of the cell wall peptidoglycan of bacteria.Selective desilylation of the muramic acid derivative 8a and formation of the α-trichloroacetimidate 28-α provided a good muramic acid glycosyl donor.With various glycosyl acceptors depending on the catalyst and the reaction conditions either β- or α-glycosides and -disaccharides were obtained selectively and in high yields.