107952-48-7

Upstream product

• 3868-03-9 1,6:2,3-dianhydro-β-D-mannopyranose 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 

Downstream Products

• 220099-50-3 1,6-anhydro-2-deoxy-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose 
• 220099-51-4 (1R,2S,3R,5R)-3-Benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6,8-dioxa-bicyclo[3.2.1]octane 

Relevant academic research and scientific papers

The chemical synthesis of a cyclic oligosaccharide derivative with branching

A cyclic oligosaccharide derivative was synthesized by cationic ring- opening polymerization of an anhydrodisaccharide derivative under high vacuum in dichloromethane with 20 mol% of PF5 as initiator. Analysis of the spectral results showed that the oligomer chain is composed of only 3 glucose units connected by α-1,6 linkages with a glucopyranosyl branching unit at C- 4 of each sugar residue in the main chain.

AUFBAU VON OLIGOSACCHARIDEN MIT GLYCOSYLFLUORIDEN UNTER LEWISSAEURE-KATALYSE

Glycosylation of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (6), as well as its 6-trimethylsilyl ether 7 with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl fluoride (5) was achieved stereospecifically in a mild and fast manner in the presence of Lewis acids like, e.g., titanium tetrafluoride, to give the β-(16)-linked disaccharide derivative 1.By use of 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride (8) or its α anomer 10 and titanium tetrafluoride in acetonitrile with 6 or 7, a fast reaction proceeds preponderantly to yield 1,2:3,4-di-O-isopropylidene 6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-galactopyranose (2).In ether, however, mainly the α-(16) anomer was formed.These model systems were used to elucidate the limiting conditions for this procedure, and mechanistic conceptions are discussed.By glycosylation at O-4 of 1,6:2,3-dianhydro-β-D-mannopyranose (11) with the perbenzylated α-fluoride 10 both the α- and the β-D-(14) disaccharide derivatives 12 and 14 were obtained, but 5 gave exclusively the β-D-(14) compound 16.Opening of the anhydro rings of 12 led to the synthesis of N-acetyl-maltosamine (22). 1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose was glycosylated with methyl (2,3,4-tri-O-acetyl-β-D-galactopyranosyl fluoride)uronate under titanium tetrafluoride catalysis to give the β-D-(13)-linked disaccharide 26, subsequently transformed into 29.