ISSN:
0170-2041
Schlagwort(e):
Fucopyranosyl phosphate
;
Fucose 1-phosphate
;
Glycosyl phosphate
;
GDP-fucose
;
Guanosine diphosphofucose
;
Trichloroacetimidates
;
Carbohydrates
;
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Reaction of the benzyl- and acetyl-protected α-trichloroacetimidates 1 and 6α with dialkyl and diaryl phosphates in the presence of traces of acid affords stereoelectively the thermodynamically more stable α-L-fucopyranosyl phosphates 2, 7 and 8, respectively, in high yields. The use of very pure, recrystallized dibenzyl phosphate results in the stereoeletive formation of the β-L-fucopyranosyl phosphates 3 and 9. In each case separation of the anomers is not required because of the very high stereoselectivity of the reactions. After deprotection the fucose 1-phosphate 12 is coupled with GMP morpholidate 10 to yield GDP-fucose 13. After the development of a new purification procedure for GDP-fucose 13 we have obtained a very pure compound suitable for biochemical investigations. Analytical and preparative HPLC has been performed on reversed-phase columns using a volatile buffer system (triethylammonium hydrogen carbonate) as the eluant.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/jlac.199119910122
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