ISSN:
0170-2041
Keywords:
Azidophytosphingosines
;
3,4-Anhydrophytosphingosines
;
Sphingosine biosynthesis
;
Enzyme inhibitors
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
2,4-O-Benzylidene-D-threose (1) was treated with the Grignard reagent obtained from n-octyl bromide to afford the epimeric tetrol derivatives 3a, b. Regioselective 2-O-mesylation and subsequent azido group introduction furnished azidophytosphingosine derivatives 5a, b. Ensuing 4-O-mesylation, acidcatalyzed benzylidene group removal and then treatment with NaH as a base provided preferentially the desired 3,4-epoxide derivatives 8a, b; subsequent azido group reduction with triphenylphosphane/water yielded the target molecules 9a, b possessing D-ribo and L-lyxo configuration, respectively.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930112
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