- Stereoselective preparation of alkyl glycosides of 2-acetamido-2-deoxy-α-D-glucopyranose by nonclassical halide-ion catalysis and synthesis and NMR spectroscopy of α-D-Gal p-(1-->3)-α-D-Glc pNAc-OMe
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Keywords: Alkyl glycosides; 2-Acetamido-2-deoxy-α-D-glucopyranose; α-D-Gal p-(1 --> 3)-α-d-GlcpNAcOMe
- Pozsgay, Vince,Coxon, Bruce
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p. 171 - 178
(2007/10/02)
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- Synthesis of methyl O-α-L-fucopyranosyl- (1 → 2)- O-β-D-galactopyranosyl- (1 → 3)- 2-acetamido- 2-deoxy-β-D-glucopyranoside, using 2,3,4-tri-O-benzoyl-α-L-fucopyranosyl bromide as the α-L-fucosylating agent
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The authors cover the synthesis of trisaccharide methyl glycosides using fucosylation. Fucopyranosyl bromide was used as the fucosylating agent. The melting point, optical rotations, and NMR spectra of these glycosides are reported.
- Nifant'ev,Shashkov,Kochetkov
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p. 331 - 336
(2007/10/02)
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- Enzymic synthesis of di- and tri-saccharide glycosides, using glycosidases and beta-D-galactoside 3-alpha-sialyl-transferase.
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The following disaccharide glycosides were obtained in yields of 10-35% from the appropriate donor and acceptor glycosides by employing glycosidases as catalysts: alpha-D-Galp-(1----3)-alpha-D-GalpNAc-OEt (alpha-D-galactosidase), beta-D-Galp-(1----3)-alpha-D-GalpNAc-OEt and beta-D-Galp-(1----3)-beta-D-GalpNAc-OEtBr (beta-D-galactosidase), beta-D-GlcpNAc-(1----6)-beta-D-Galp-OMe and beta-D-GlcpNAc-(1----6)-alpha-D-Manp-OMe (beta-N-acetylglucosaminidase). With beta-D-GlcpNAc-OEtSiMe3 as the acceptor, beta-D-galactosidase gave beta-D-Galp-(1----3)-beta-D-GlcpNAc-OEtSiMe3 almost exclusively, whereas, with beta-D-GlcpNAc-OMe as the acceptor, beta-D-Galp-(1----3)-beta-D-GlcpNAc-OMe was formed in only slightly excess over teh analogous beta-(1----4)-linked glycoside. The use of beta-D-galactosidase and beta-D-galactoside 3-alpha-sialyltransferase in sequence provided a convenient route to the trisaccharide glycosides alpha-D-Neup5Ac-(2----3)-beta-D-Galp-(1----3)-alpha-D-GalpNAc-OEt, alpha-D-Neup5Ac-(2----3)-beta-D-Galp-(1----3)-beta-D-GalpNAc-OE tBr, and alpha-D-Neup5Ac-(2----3)-beta-D-Galp-(1----3)-beta-D-GlcpNAc-OMe.
- Nilsson
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