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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