ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Mannosylidenation of buckminsterfullerene (C60; 1) with the 2,3-di-O-benzyl-4,6-O-benzylidene-protected diazirine 7 and the 2,3:4,6-di-O-isopropylidene-protected diazirine 8 leads to the spiro-linked C -glycosides 6 and 10 in 44 and 31% yield, respectively (Scheme). The diazirine 8 was prepared in five steps from 2,3:4,6-di-O-iso-propylidene-α-D-mannopyranose (11) via the oximes 12, the (Z)-hydroximolactone 13, the mesylate 14, and the diaziridines 15. Deprotection of the mannosylidenated fullerenes 6 and 10 under acidic conditions gave the partially deprotected diol 9 (97%) and the unprotected mannosylidenated fullerene 16 (73%), respectively. The mannosylidene-fullerenes 6, 9, 10, and 16 possess a 6-6 ring-bridged σ-homoaromatic structure.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19940770820
Permalink