ISSN:
0170-2041
Keywords:
Carbohydrates
;
Hexofuranoses
;
3, 6-Anhydro-D-hexofuranoses
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis, Structure Elucidation and Reactions of trans-Fused 3, 6-Anhydro-1, 2-O-isopropylidene-α-D-hexofuranosesUnexpectedly, the reaction of 1, 2-O-isopropylidene-5, 6-di-O-(p-tolylsulfonyl)-α-D-allofuranose (7) with KCN in ethanol yielded the first trans-fused 3,6-anhydro-hexofuranose 10. Besides by spectroscopic evidence the structure of 10 was proved by transformation to the tosylated acetal 13 which could also be obtained via an independent route. Further reactions of 10 all resulted in opening of the strained ring system yielding acetals (18-22). By blocking the 5-position with the alkali-resistant ether function this cyclization could also be achieved by more common reagents like NaH in DMF (32). - By applying this procedure to the corresponding α-D-galactofuranose derivative 41 3,6-anhydro-α-D-galactofuranose 42 could also be obtained albeit in low yield. For comparison purposes the 3,6-anhydro-α-D-gulo derivative 47 was synthesized from easily accessible 44.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940405
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