ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Some reactions of 3-O-alkyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-uloses (1 and 2) with Wittig reagents are described. These ketosugars react with methylenetriphenylphosphorane and benzylidenetriphenylphosphorane to give the expected unsaturated branched-chain sugars and dienes formed by elimination of H-C(4) and the 3-alkyloxy group. Structural studies on all these compounds have been effected using NMR. spectroscopy and particularly, when necessary, nuclear Overhauser Effect. One important by-product of these reactions is an unsaturated ketone 3,6-dideoxy-1,2-O-isopropylidene-α-D-glycero-hex-3-enofuranos-5-ulose (6). Compounds 1 and 2 do not react with cyanomethylenetriphenylphosphorane.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19750580531
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