In:
Helvetica Chimica Acta, Wiley, Vol. 74, No. 2 ( 1991-03-13), p. 315-322
Abstract:
The glycosylation of indazolyl anions derived from 4a , b with 2‐deoxy‐3,5‐bis‐ O ‐(4‐methylbenzoyl)‐α‐ D ‐ erythro ‐pentofuranosyl chloride ( 5 ) is described. The reaction was Stereoselective – exclusive β‐ D ‐anomer formation – but regioisomeric N 1 ‐ and N 2 ‐(2′‐deoxy‐β‐ D ‐ribofuranosides) ( i.e. 6a and 7a , resp., and 6b and 7b , resp.) were formed in about equal amounts. They were deprotected to yield 8a , b and 9a , b . Compound 1 , related to 2′‐deoxyadenosine ( 3 ), and its regioisomer 2 were obtained from 8b and 9b , respectively, by catalytic hydrogenation. The anomeric configuration as well as the position of glycosylation were determined by 1D NOE‐difference spectroscopy. The first protonation site of 1 and 2 was found to be the NH 2 group. The N ‐glycosylic bond of 1 H ‐indazole N 1 ‐(2′‐deoxyribofuranosides) is more stable than that of the parent purine nucleosides. Compound 1 is no substrate for adenosine deaminase.
Type of Medium:
Online Resource
ISSN:
0018-019X
,
1522-2675
DOI:
10.1002/hlca.19910740209
Language:
English
Publisher:
Wiley
Publication Date:
1991
detail.hit.zdb_id:
74-7
detail.hit.zdb_id:
1475013-2
