A comparative study of different glycosylation methods for the synthesis of D-mannopyranosides of Nalpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester.
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.
Lee
Dong Jun
DJ
Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
Kowalczyk
Renata
R
Muir
Victoria J
VJ
Rendle
Phillip M
PM
Brimble
Margaret A
MA
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
D000596:Amino Acids; D002241:Carbohydrates; D004952:Esters; D005449:Fluorenes; D037102:Lectins; C525838:N2-fluorenylmethoxycarbonyl-4-hydroxyproline allyl ester; D011714:Pyrans; D011392:Proline; D008358:Mannose