ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A route for synthesizing C-nucleosides with 2,6-substituted pyridines as heterocyclic aglycones is described. Condensation of appropriately substituted lithiated pyridines with ribono-1,4-lactone derivatives yields hemiacetal 4a-g (Table 1), which can be reduced by Et3SiH and BF3·Et2O to the corresponding C-nucleoside (see Scheme 1 for 4d → β-D-5). Conditions are presented that optimize the amount of the 2,6-dichloropyridine-derived β-D-anomer β-D-5 formed (Table 3). Aminolysis of β-D-5 yields the diaminonucleoside 14 (Scheme 3).
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19910740217
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