title: A comparative study of different glycosylation methods for the synthesis of D-mannopyranosides of Nalpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester.
abstract: The synthesis of Nalpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-acetyl)-alpha-d-mannopyranosyl]-l-proline allyl ester and Nalpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzoyl)-alpha-d-mannopyranosyl]-l-proline allyl ester is described. Glycosylation using Königs-Knorr conditions with a benzoyl protected glycosyl donor provided the optimum method. Removal of the allyl ester gave two mannosylated building blocks suitable for solid phase glycopeptide synthesis.
authors.affiliation: Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
authors.forename: Dong Jun
authors.initials: DJ
authors.lastname: Lee
authors.forename: Renata
authors.initials: R
authors.lastname: Kowalczyk
authors.forename: Victoria J
authors.initials: VJ
authors.lastname: Muir
authors.forename: Phillip M
authors.initials: PM
authors.lastname: Rendle
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry; D002621:Chemistry / Q000379:methods*; D004952:Esters / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis*; D006031:Glycosylation; D037102:Lectins / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000737:chemistry; D008956:Models, Chemical; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D013053:Spectrophotometry / Q000379:methods
chemical_list: D000596:Amino Acids; D002241:Carbohydrates; D004952:Esters; D005449:Fluorenes; D037102:Lectins; C525838:N2-fluorenylmethoxycarbonyl-4-hydroxyproline allyl ester; D011714:Pyrans; D011392:Proline; D008358:Mannose