In:
Helvetica Chimica Acta, Wiley, Vol. 74, No. 2 ( 1991-03-13), p. 397-406
Abstract:
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 Et 3 SiH and BF 3 ·Et 2 O 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 ).
Type of Medium:
Online Resource
ISSN:
0018-019X
,
1522-2675
DOI:
10.1002/hlca.19910740217
Language:
English
Publisher:
Wiley
Publication Date:
1991
detail.hit.zdb_id:
74-7
detail.hit.zdb_id:
1475013-2
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