119237-90-0

Upstream product

• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 100-39-0 benzyl bromide 
• 81600-93-3 allyl 4,6-di-O-benzylidene-α-D-mannopyranoside 
• 214490-84-3 Allyl 2,3,4,6-Tetra-O-acetyl-D-mannopyranoside 
• 182212-07-3 α,β-O-allyl-D-mannopyranoside 
• 119111-33-0 (3aS,5aR,8R,9aR,9bS)-4-Allyloxy-2,8-diphenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine 

Downstream Products

• 1144104-04-0 allyl 3-O-benzyl-4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 97576-68-6 (2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol 
• 1186302-39-5 allyl 4,6-O-benzylidene-3-O-benzyl-2-O-9-fluorenylmethyloxycarbonyl-α-D-mannopyranoside 
• 165061-00-7 allyl 3-O-benzyl-2,6-bis-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 165061-03-0 allyl 2-O-acetyl-3-O-<4,6-di-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-benzyl-α-D-mannopyranosyl>-4,6-O-benzylidene-α-D-mannopyranoside 
• 165061-04-1 allyl 2-O-acetyl-3-O-<4,6-di-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-benzyl-α-D-mannopyranosyl>-α-D-mannopyranoside 
• 165061-01-8 propyl 2,6-bis-O-(2-acetamido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-α-D-mannopyranoside 
• 165061-09-6 O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl trichloroacetimidate 
• 165061-07-4 allyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-4,6-di-O-acetyl-3-O-benzyl-α-D-mannopyranoside 
• 165061-08-5 O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-2,4-di-O-acetyl-3-O-benzyl-α-D-mannopyranoside 
• 165060-99-1 allyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-α-D-mannopyranoside 
• 119111-10-3 Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2R)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester 
• 20770-84-7 2,3-di-O-benzyl-4,6-O-benzylidene-α/β-D-mannopyranose 
• 119237-93-3 (R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-manno-hept-1-enitol 

Relevant academic research and scientific papers

Synthesis of |β-(1→2)-linked oligomannosides

β-(1→2)-Linked oligomannosides constitute an important class of carbohydrate structures located on the cell surface of several Candida species, including C. albicans. As a result of the immunostimulating properties of such compounds, the upscaling of their synthesis is relevant. In this paper, a highly stereoselective synthesis of |β-(1→2)-linked oligomannosides was performed by further development of and modifications to the methodologies described earlier in the literature. In addition to the synthesis of fully deprotected β-(1→2)-linked mannobiose and mannotriose, some preliminary modifications to the oligosaccharide core, resulting in close analogues with biological potential, are presented. The fully deprotected products form potential targets for screening against C. albicans and may also result in new model structures for vaccine development.

Synthesis of a sialic acid containing complex-type n-glycan on a solid support

A new solid-phase synthesis of N-linked glycans featuring 1) highly ste-reoselective b-mannosylation and microfluidic a-sialylation and 2) efficient glycosylation of the N-phenyltrifluoroacetimidate units on JandaJel resin is reported. Reagent concentration effects by a fluorous solvent are effectively applied, and the use of these methods results in the first synthesis of a sialic acid containing complex-type N-glycan on a solid support.

Enzymic transfer of 6-modified D-galactosyl residues: Synthesis of biantennary penta- and hepta-saccharides having two 6-deoxy-D-galactose residues at the nonreducing end and evaluation of 6-deoxy-D-galactosyl transfer to glycoprotein using bovine β-(1 4)-galactosyltransferase and UDP-6-deoxy-D-galactose

UDP-6-Deoxy-D-galactose and UDP-6-deoxy-6-fluoro-D-galactose were synthesized and their transfer to 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine) by β-(1 → 4)-galactosyltransferase was examined. The transfer rates of 6-deoxy-D-galactose and 6-deoxy-6-fluoro-D-galactose were 1.3 and 0.2% of that of D-galactosyl transfer, respectively. The 2-acetamido-4-O-(6-deoxy-β-D-galactopyranosyl)-2-deoxy-D-glucopyranos e (6'-deoxy-N-acetyllactosamine) and methyl 2-acetamido-4-O-(6-deoxy-6-fluoro-β-D-galactopyranosyl)-2-deoxy-D-glu copyranoside (6'-deoxy-6'-fluoro-N-acetyllactosamine) were synthesized enzymatically in 30 and 59% yields, respectively. Further, 6-deoxy-D-galactose could be completely transferred to N-linked type biantennary oligosaccharides having two N-acetyl-D-glucosaminyl residues at the nonreducing end to give the corresponding penta- and hepta-saccharides in 55 and 57% yields, respectively. An assay of 6-deoxy-D-galactosyl transfer using asialo agalacto α1-acid glycoprotein as an acceptor suggested that 6-deoxy-D-galactose was transferred to about 30% of the N-acetyl-D-glucosaminyl residues in the N-linked oligosaccharides of the glycoprotein.

Stereochemical Control in Hex-5-enyl Radical Cyclizations: From Carbohydrates to Carbocycles. 3

The hex-5-enyl radical cyclization reaction was applied to prepare highly oxygenated cyclopentanoids from aldopyranose sugars.The Wittig reaction of the sugars readily provides hex-5-en-1-ols which were converted to hex-5-enyl radicals via one of the vari