ISSN:
0170-2041
Keywords:
Phytosphingosines
;
Azides
;
Sphingosines
;
Dodec-5-enes
;
Dodec-5-ynes
;
Tetrols
;
Epoxides
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Reaction of the lithium acetylide prepared from bromooctene 2 with 2,4-O-benzylidene-D-threose (1) yielded the epimeric dodec-5-ynetetrol derivatives 3a, b. Reaction of the Grignard reagent of bromooctene 2 with 1 gave (E,Z)-dodec-5-ene-tetrol derivatives (E,Z)-12a,b. From these precursors D-ribo-phytosphingosine derivatives 7b, (E)-18, and (Z)-18, respectively, were obtained. Also interesting anhydro derivatives, for instance 3,4-epoxides 11a and (E)-21, and 1,4-anhydro phytosphingosine derivatives 9a, 10a, and (E)-23, respectively, were synthesized. A very useful method is described for the assignment of the configuration at C-4 of the 1,3-O-benzylidene-1,2,3,4-tetrol derivatives 3a, 3b, (E,Z)-12a, and (E,Z)-12b by means of NMR spectroscopy.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940115
