79781-68-3

Upstream product

• 90405-18-8 Allyl-2-azido-2-desoxy-β-D-galactopyranosid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 
• 108-24-7 acetic anhydride 
• 100-39-0 benzyl bromide 
• 79781-69-4 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose 
• 127-09-3 sodium acetate 
• 94715-75-0 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl nitrate 
• 97604-18-7 allyl-2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-galactopyranosid 

Downstream Products

• 67313-39-7 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-galactopyranose 
• 79781-70-7 4-Nitro-benzoic acid (3R,4R,5R,6R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 79781-69-4 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose 
• 79781-71-8 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl bromide 
• 59464-22-1 1,6-anhydro-2-azido-2-deoxy-3,4-di-O-benzyl-β-D-galactopyranose 
• 443915-92-2 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-gluco-oct-1-ynitol 
• 443916-32-3 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-L-gluco-oct-1-ynitol 
• 79781-67-2 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl chloride 
• 79781-74-1 benzyl O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1-3)-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-(1-3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 

Relevant academic research and scientific papers

Conversion of glycals into vicinal-1,2-diazides and 1,2-(or 2,1)-azidoacetates using hypervalent iodine reagents and Me3SiN3. Application in the synthesis of: N -glycopeptides, pseudo-trisaccharides and an iminosugar

Glycals were found to react with a reagent system comprising of phenyliodine bis(trifluoroacetate) (PIFA) and Me3SiN3 in the presence of TMSOTf as a catalyst to form the corresponding vicinal 1,2-diazides. On the other hand, they rea

Synthesis of α- and β-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling

A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of α- or β-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-α-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of α- and β-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.

THE SYNTHESIS OF 2-AZIDO C-GLYCOSYL SUGARS

2-Azido C-glycosyl sugars can be prepared by the Lewis acid catalyzed addition of alkyl silanes to the nitrate glycosides of 2-azido sugars.The products are ozonized to the corresponding aldehydes for further elaboration.

SYNTHESE DER TETRA- UND TRISACCHARID-SEQUENZEN VON ASIALO-GM1 UND -GM2. LENKUNG DER REGIOSELEKTIVITAET DER GLYCOSIDIERUNG VON LACTOSE

A regioselective β-glycosidation of lactose derivatives unsubstituted at OH-3' and -4' is possible, depending on the catalyst system applied.With silver silicate or silver carbonate as catalyst under hetrogeneous conditions, β-glycosidation occured selectively at the less reactive OH-4'group of the acceptor, whereas with trimethylsilyl triflate or soluble mercury salt as catalyst under homogeneous conditions, it occured almost exclusively at the more reactive OH-3' group.The reactivity of the glycosyl donor, acceptor, and catalyst had to be properly matched for successful regioselective coupling.In this way, the trisaccharide unit of asialo-GM2-ganglioside, O-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1--4)-(β-D-galactopyranosyl-(1--4)-D-glucopyranose, and the tetrasaccharide unit of asialo-GM1-ganglioside, O-(β-D-galactopyranosyl)-(1--3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1--4)-(β-D-galactopyranosyl)-(1--4)-β-D-glucopyranose were synthesized.This new method constitutes a very useful approach in the field of ganglioside synthesis.