3'-DEOXY-3'-HYDROXYMETHYL-ALDOPENTOPYRANOSYL NUCLEOSIDE SYNTHESIS .1.

被引：13

作者：

DOBOSZEWSKI, B

BLATON, N

ROZENSKI, J

DEBRUYN, A

HERDEWIJN, P

机构：

[1] CATHOLIC UNIV LEUVEN,REGA INST MED RES,MED CHEM LAB,B-3000 LOUVAIN,BELGIUM

[2] CATHOLIC UNIV LEUVEN,FAC PHARM,ANALYT CHEM LAB,B-3000 LOUVAIN,BELGIUM

[3] STATE UNIV GHENT,DEPT ORGAN CHEM,B-9000 GHENT,BELGIUM

来源：

TETRAHEDRON | 1995年 / 51卷 / 18期

关键词：

D O I：

10.1016/0040-4020(95)00211-P

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward synthesis of 3'-deoxy-3'-hydroxymethyl-aldopentopyranosyl nucleosides is described starting from beta-D-xylopyranosyl nucleosides. beta-D-xylopyranosyl thymine 17a,b,c and uracil 17d are converted into the 4'-benzoylated derivatives 18a,b and further into the 2',3'-enepyranosyl compounds 19b,c. A 3'-hydroxymethyl appendix has been introduced using a free-radical methodology to furnish 20a,b. Inversion of configuration of the 4'-position yielded the target nucleosides 22a,b. X-ray and H-1 NMR conformation analysis prove the equatorial orientation of the base moiety in the target compounds.

引用

页码：5381 / 5396

页数：16

共 32 条

[1]

Herdewijn, Doboszewski, De Winter, Verheggen, Augustyns, Hendrix, Saison-Behmoaras, De Ranter, Van Aerschot, Carbohydrates, synthetic methods and applications in antisense therapeutics, American Chemical Society Symposium Series, (1994)

[2]

Eschenmoser, Proceedings of the Robert A. Welch Foundation, 37th Conference on Chemical Research: 40 years of the DNA double helix, (1993)

[3]

Van Aerschot, Verheggen, Herdewijn, Bioorg. Med. Chem. Lett., 3, pp. 1013-1018, (1993)

[4]

Verheggen, Van Aerschot, Toppet, Snoeck, Janssen, Claes, Balzarini, De Clercq, Herdewijn, J. Med. Chem., 36, pp. 2033-2240, (1993)

[5]

Herdewijn, Antiviral Chemistry and Chemotherapy, 5, pp. 131-146, (1994)

[6]

Ferrier, Adv. Carbohydr. Chem. Biochem., 24, pp. 199-266, (1969)

[7]

Ferrier, Adv. Carbohydr. Chem. Biochem., 20, pp. 67-137, (1965)

[8]

Bessodes, Egron, Filippi, Antonakis, Synthesis of unsaturated 4?-azido pyranosyl thymines as potential antiviral and anti-HIV agents, Journal of the Chemical Society, Perkin Transactions 1, pp. 3035-3039, (1990)

[9]

Khripatsh, Mikhalopulo, Akhryem, Khim. Getero. Soedin., pp. 111-117, (1982)

[10]

Fuentes, Garcia-Munoz, Madronero, Stud, Rico, Tetrahedron, 26, pp. 4823-4837, (1970)

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