ISSN:
0170-2041
Keywords:
Allylation, indium-assisted
;
Aldoheptoses
;
Catalytic osmylation
;
Indium-assisted allylation
;
Carbohydrates
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Starting with unprotected D-pentoses 1-4 we achieved a chain elongation reaction by utilizing indium-assisted allylation. After acetylation, the polyol derivatives 1a-4a were transformed into the corresponding α,β-unsaturated aldehydes 1b-4b. Protection of the carbonyl group yielded the diethyl acetals 1c-4c. Subsequent dihydroxylation of the double bond by catalytic osmylation followed by acetylation of the newly introduced hydroxyl functions gave a mixture of diastereomeric products. However, only those diastereomers could be easily separated by column chromatography which were derived from 1c and 2c, giving access to D-glycero-D-galacto and D-glycero-L-galacto precursor 5 and 7, respectively. Final deprotection yielded the title aldoheptoses 6 and 8.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940113
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