ISSN:
0170-2041
Keywords:
D-Glucofuranurono-6,3-lactone
;
Reformatsky reaction
;
7-Deoxyoctoses
;
Castanospermine
;
Glycosidase inhibitors
;
Carbohydrates
;
Enzymes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of (+)-Castanospermine and 1-Epicastanospermine from D-Glucofuranurono-6,3-lactone by Reformatsky ReactionStarting from 5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-gluco- (2a) or -β-L-idofuranurono-6,3-lactone (2b), 7-deoxyoctofuranose derivatives 5a, 5b, 7a and 7b have been synthesized by chain extension at C-6 by Reformatsky reaction followed by reduction with calcium borohydride. The respective configuration of the products was determined by transformation into the known 7,8-dideoxyoctofuranoses 5o, 5p, 7k and 7l. From the mixture of 7a and 7b, formed in a proportion of approximately 4:1, the glycosidase inhibitors (+)-castanospermine (1a) and 1-epicastanospermine (1b) have been prepared in 8 and 9 simple steps, respectively, in overall yields of 33.4 and 9.5%.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930164
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