Synthese von Azaanalogen der Ascorbinsäure und der Isoascorbinsäure

Autor:	Hans-Dietrich Stachel, Hermann Lotter, Klaus Zeitler
Rok vydání:	1994
Předmět:	chemistry.chemical_compound chemistry Aldol reaction Stereochemistry Organic Chemistry Tetramic acid Physical and Theoretical Chemistry Ascorbic acid Derivative (chemistry) Adduct Catalysis
Zdroj:	Liebigs Annalen der Chemie. 1994:1129-1134
ISSN:	1099-0690 0170-2041
DOI:	10.1002/jlac.199419941113
Popis:	Synthesis of Azaanalogues of Ascorbic Acid and Isoascorbic Acid The synthesis of the hitherto unknown azaanalogues of ascorbic acid (±)-10b and isoascorbic acid (±)-10a is described. The aldol-type reaction of the tetramic acid derivative 4 with benzyloxyacetaldehyde gives rise to a mixture of the adducts (±)-5a and (±)-5b. By X-ray analysis 5b proved to represent the threo isomer. Catalytic debenzylation of both adducts 5 to the glycols 9 was successful only with 5a leading to 9a. On the other hand, both isomers (±)-9a and (±)-9b have been obtained from the aldols 6a/6b by successive debenzylation and desilylation. Removal of the remaining protective group from 9a/9b yielded racemic N-benzylazaisoascorbic acid and racemic N-benzylazaascorbic acid, respectively.
Databáze:	OpenAIRE
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