ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Methyl 2,5:3,6-Dianhydro-D-mannofuranosidesMonotosylation of methyl 3,6-anhydro-β-D-glucofuranoside gives as minor reaction product 1 which yields by treatment with sodium ethanolate methyl 2,5 : 3,6-dianhydro-β-D-mannofuranoside (2). The α-anomer 6 is equally prepared from 3 which is obtained by selective monotosylation of methyl 3,6-anhydro-β-L-gulofuranoside. Reaction of methyl 3,6-anhydro-2,5-di-O-tosyl-α-D-glucofuranoside (5) gives only small amounts of 6 accompanied by the monotosylate 4. Mass and NMR spectra (2D-1H and 13C) of the new dianhydrides 2 and 6 are described.
Notes:
Monotosylierung von Methyl-3,6-anhydro-bT-D-glucofuranosid ergibt als Nebenprodukt 1, dessen Behandlung mit Natrium-ethanolat zum Methyl-2,5 : 3,6-dianhydro-β-D-mannofuranosid (2) führt. Das entsprechende α-Anomere 6 kann analog aus 3, dem Produkt der selektiven Monotosylierung des Methyl-3,6-anhydro-β-L-gulofuranosids erhalten werden. Hingegen liefert die Umsetzung des Methyl-3,6-anhydro-2,5-di-O-tosyl-α-D-glucofuranosids (5) nur geringe Mengen 6 neben Monotosylat 4. Die NMR-Spektren (2D-1H und 13C) sowie der massenspektrometrische Zerfall der neuen Dianhydride 2 und 6 werden beschrieben.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198319830807
