ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The tetrazole 1 is a new β-glucosidase inhibitor (IC50=8·10-5 M, Emulsin), obtained (92%) by deprotection of 22, the product of an intramolecular cycloaddition of the azidonitrile 20. This azidonitrile was formed as an intermediate by treating the L-ido-bromide 14 or the L-ido-tosylate 19 with NaN3 at 110-120°. It was isolated in a separate experiment. The yield of 22 from 19 reached 70%; 21 was formed as by-product (10%). The bromide 14 (42%) and the iodide 15 (30-35%) were obtained from the nitrile 13, together with the 2,5-anhydro-L-idononitrile 16, which was formed in ca. 35-45%. The tosylate 19 was obtained from 18 (97%). To obtain 18, the nitrile 13 was oxidized according to Swern (→17, 92%) and then reduced (NaBH4, CeCl3), leading to 18and 13 (92%, 18/13 93:7). Reduction of the tetrahydropyridotetrazole 22 with LiAlH4 afforded 83 % of the piperidine 23, which was deprotected to (+)-1-deoxynojirimycin hydroacetate (2·AcOH, 86%) and further converted into the corresponding hydrochloride and into the free base 2.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19910740839
