ISSN:
0170-2041
Keywords:
Sphingosines
;
Azidosphingosines
;
Octadec-4-enes
;
Enzymes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Treatment of 2,4-O-benzylidene-D-threose (3) with the Wittig reagent obtained from 2-bromopentadecane furnished 5-methyloctadec-4-ene derivatives (E,Z)-8. The introduction of the azido group into the 2-position and acid-catalyzed removal of the benzylidene protective group afforded 5-methyl-substituted azidosphingosines (E)-10 and (Z)-10 which were converted via azide reduction into the corresponding sphingosines (E)-1 and (Z)-1, respectively. Reaction of 3 with methylmagnesium bromide, ensuing selective 2-O-mesylation, and then 4-O-oxidation gave ketone 13. The Wittig reaction of 13 with triphenyltetradecylphosphorane afforded exclusively 4-methyloctadec-4-ene derivative (Z)-16 which was transformed into 4-methyl-substituted sphingosine (Z)-2 as described above. For the synthesis of the corresponding E isomer, 3 was converted into carbinols 21h,l. 2-O-Silyl protection and then water elimination furnished 4-methyl-substituted (4E)-octadec-4-ene derivative (E)-23 which was transformed into (E)-2.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930168
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