The Efficient, Enantioselective Synthesis of Aza Sugars from Amino Acids. 1. The Polyhydroxylated Pyrrolidines
- 1 January 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (2) , 372-376
- https://doi.org/10.1021/jo962028s
Abstract
Beginning with (+)-serine or (−)-serine, as appropriate, convenient, high-yield, enantioselective synthesis of all eight stereoisomeric 2-hydroxymethyl-3,4-dihydroxypyrrolidines (the enantiomeric pairs of iminoribitol, -arabinitol, -xylitol, and -lyxitol) can be effected. The absolute configuration of the starting amino acid defines the set of azasugars produced.Keywords
This publication has 19 references indexed in Scilit:
- Trypanosomal Nucleoside Hydrolase. Resonance Raman Spectroscopy of a Transition-State Inhibitor ComplexBiochemistry, 1996
- Five-membered ring azasugars as potent inhibitors of α-L-rhamnosidase (naringinase) from Penicillium decumbensBioorganic & Medicinal Chemistry, 1994
- Amidrazone Analogs of D-Ribofuranose as Transition-State Inhibitors of Nucleoside HydrolaseBiochemistry, 1994
- Use of dihydroxyacetone phosphate-dependent aldolases in the synthesis of deoxy aza sugarsThe Journal of Organic Chemistry, 1991
- An ab initio study (6-31G*) of transition states in glycoside hydrolysis based on axial and equatorial 2-methoxytetrahydropyransJournal of the American Chemical Society, 1991
- Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: synthesis, evaluation, and modeling of glycosidase inhibitorsJournal of the American Chemical Society, 1991
- Catalytic mechanism of enzymic glycosyl transferChemical Reviews, 1990
- Potential glycosidase inhibitors: synthesis of 1,4-dideoxy-1,4-imino derivatives of D-glucitol, D- and L-xylitol, D- and L-allitol, D- and L-talitol, and D-gulitolJournal of the Chemical Society, Perkin Transactions 1, 1990
- Synthesis of (2R,3S,4S)-3,4-dihydroxy-2-hydroxymethylpyrrolidine and polyoxamic acid derivatives from (S)-pyroglutamic acid.CHEMICAL & PHARMACEUTICAL BULLETIN, 1989
- Useful syntheses of erythro- and threo-N-oleoyl-D-sphingosines (ceramides) and galactosylceramides (cerebrosides) from L-serineThe Journal of Organic Chemistry, 1981