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A Novel and Efficient Route towards α-GalNAc-Ser and α-GalNAc-Thr Building Blocks for Glycopeptide Synthesis (1999)

Winterfeld, Gottfried A. ; Ito, Yukishige ; Ogawa, Tomoya ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 1167-1171

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ISSN: 1434-193X

Keywords: Carbohydrates ; Glycals, nitro ; Michael additions ; Glycosylations ; Glycosides, galactosamine ; Reduction, nitro group ; Glycopeptides ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: -Michael addition of serine and threonine derivatives 4a-4c to 3,4,6-tri-O-benzyl-2-nitro-D-galactal (1) afforded the corresponding 2-deoxy-2-nitro-α-D-galactopyranosides 5a-5c in good yield and stereoselectivity. 2-deoxy-2-nitroglycosides 5a and 5b were reduced to the 2-acetamido compounds by platinized Raney nickel T4. Manipulation of the protecting groups afforded known N-Fmoc-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine (8a) and -threonine (8b), valuable building blocks for O-glycopeptide synthesis.

Type of Medium: Electronic Resource

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