Format:
Online-Ressource
ISSN:
1522-2675
Content:
Abstract: The d‐manno‐configured N‐anisylated β‐lactam 40, the β‐lactam carboxylic acids 4 and 43, and the corresponding phosphonic‐acid isosters 49 and 50 have been synthesized from d‐glucose in 8 – 10 steps, respectively. None of these compounds exhibited a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, Influenza A (N9), and Influenza B virus. Cycloaddition of the in situ generated imines derived from the d‐erythroses 6, 16, and 17 with the ketene from mesyloxyacetyl chloride (20) gave the 2‐mesyloxy‐d‐hexono‐1,3‐lactams 25, 27a/b, 28a/b/c, and 29 in 23, 69, 57, and 90% yield, respectively (Scheme 3). Transformation of 27a/b and 29 (〉85%) to the corresponding azides, followed by oxidative N‐deprotection, gave 30a/b (45%) and 34 (80%). Subsequent alkylation of the ring N‐atom in 31a with benzyl bromoacetate and dibenzyl (triflyloxymethyl) phosphonate 46 gave the carboxylate 41 (77%) and the phosphonate 47 (55%; Schemes 4 and 5). Hydrogenolysis of 41 gave the β‐lactam amino acid 43, besides its hydrolysis product 44. Reductive N‐acylation of the azido group in 41 (93%), followed by hydrogenolytic debenzylation, yielded the 2‐trifluoroacetamido N‐(carboxymethyl)‐β‐lactam 4 (56%). Similarly, 47 gave the 2‐trifluoroacetamide 48 (89%), and hence, the 2‐amino‐N‐(phosphonoylmethyl)‐β‐lactams 49 (40%) and 50, resulting from deacylation of 49 (14%). Aminolysis and carbamoylation of the protected β‐lactams 31a and 35 led to the 2,3‐diamino‐2,3‐dideoxy‐d‐mannonamides 51 and 53, respectively (Scheme 6).
In:
volume:82
In:
number:12
In:
year:1999
In:
pages:2380-2412
In:
extent:33
In:
Helvetica chimica acta, New York, NY : Wiley-VCH, 1918-, 82, Heft 12 (1999), 2380-2412 (gesamt 33), 1522-2675
Language:
English
DOI:
10.1002/(SICI)1522-2675(19991215)82:12〈2380::AID-HLCA2380〉3.0.CO;2-P
URN:
urn:nbn:de:101:1-2023112405270695059682
URL:
https://doi.org/10.1002/(SICI)1522-2675(19991215)82:12〈2380::AID-HLCA2380〉3.0.CO;2-P
URL:
https://nbn-resolving.org/urn:nbn:de:101:1-2023112405270695059682
URL:
https://d-nb.info/1310991987/34
URL:
https://doi.org/10.1002/(SICI)1522-2675(19991215)82:12〈2380::AID-HLCA2380〉3.0.CO;2-P
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