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Synthetic mucin fragments: benzyl 2-acetamido-3-O-[3-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-β-d-galactopyranosyl]-2-deoxy-α-d-galactopyranoside

✍ Scribed by Saeed A. Abbas; Khushi L. Matta


Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
274 KB
Volume
132
Category
Article
ISSN
0008-6215

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✦ Synopsis


In a continuing program for the synthesis of oligosaccharides that occur as part of mutinous glycoconjugates, we previously described* the synthesis of the disaccharide methyl 3-0-(2-acetamido-2-deoxy-P-D-glucopyranosyl)-a-D-galactopyranoside

(1). We have also demonstrated that 1 could be readily converted into its per-0-acetylated glycosyl bromide (2), the glycosylating capability of which was exemplified by the synthesis of p-nitrophenyl 2-acetamido-2-deoxy-3-O-B-Dglucopyranosyl-P-D-ga1actopyranoside3.


📜 SIMILAR VOLUMES


Synthesis of benzyl 2-acetamido-2-deoxy-
✍ Conrad F. Piskorz; Saeed A. Abbas; Khushi L. Matta 📂 Article 📅 1984 🏛 Elsevier Science 🌐 English ⚖ 428 KB

Condensation of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-a-D-galactopyranoside with 2,3,4-tri-o-acetyl-a-D-fucopyranosyl bromide in 1: 1 nitromethane-benzene, in the presence of powdered mercuric cyanide, afforded benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-0-(2,3,4-tri-O-acetyl-P-D-fucopyran

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Halide-assisted glycosyIation, using a non-p~icipating Z-substituent (benzyl) in the glycosyl halide, was used to obtain the ~-D-gaiactosyl linkage and silver triflate promotion with a participating 2-substituent (benzoyl) was used to obtain the /3-D-galactosyl linkage in a facile synthesis of the t