HALO SUGAR NUCLEOSIDES .6. SYNTHESIS OF SOME 5'-DEOXY-5'-IODO AND 4',5'-UNSATURATED PURINE NUCLEOSIDES

被引：41

作者：

DIMITRIJEVICH, SD ^{[1
]}

VERHEYDEN, JPH ^{[1
]}

MOFFATT, JG ^{[1
]}

机构：

[1] SYNTEX RES CORP, INST MOLEC BIOL, PALO ALTO, CA 94304 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 03期

关键词：

D O I：

10.1021/jo01317a019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of the 5''-hydroxyl groups of suitably substituted purine nucleosides with methyltriphenoxyphosphonium iodide in nonpolar solvents such as tetrahydrofuran and dichloromethane give the corresponding 5''-deoxy-5''-iodo nucleosides in high yield. Previously, N3,5''-cyclonucleosides were the major products of these reactions when DMF [dimethylformamide] was used as solvent. Efficient syntheses of 9-(5-deoxy-.beta.-D-erythro-pent-4-enofuranosyl) purine nucleosides are described via dehydrohalogenation of various 5''-deoxy-5''-iodoinosine, -guanosine, and -adenosine derivatives with either silver fluoride in pyridine or 1,5-diazabicyclo[4.3.0]non-5-ene in DMF or pyridine.

引用

页码：400 / 406

页数：7

共 23 条

[1] NUCLEOPHILIC REACTIVITY [J].

BUNNETT, JF .

ANNUAL REVIEW OF PHYSICAL CHEMISTRY, 1963, 14 :271-&

[2]

FIESER LF, 1968, REAGENTS ORGANIC SYN, V1, P4

[3] SYNTHESIS OF 6'-CYANO-6'-DEOXYHOMOADENOSINE-6'-PHOSPHONIC ACID AND ITS PHOSPHORYL AND PYROPHOSPHORYL ANHYDRIDES AND STUDIES OF THEIR INTERACTIONS WITH ADENINE-NUCLEOTIDE UTILIZING ENZYMES [J].

HAMPTON, A ;

SASAKI, T ;

PAUL, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (13) :4404-4414

[4] SYNTHESIS OF 5'-SUBSTITUTED DERIVATIVES OF INOSINE [J].

HAMPTON, A ;

BAYER, M ;

GUPTA, VS ;

CHU, SY .

JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (06) :1229-&

[5]

HARRIS GS, 1968, TETRAHEDRON LETT, P37

[6] A new unsaturated anhydro-glucose. [J].

Helferich, B ;

Himmen, E .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1928, 61 :1825-1835

[7]

HOLMES RE, 1963, J ORG CHEM, V28, P3483, DOI 10.1021/jo01047a050

[8] FURANOID VINYL ETHERS [J].

HOUGH, L ;

OTTER, B .

CHEMICAL COMMUNICATIONS, 1966, (06) :173-&

[9] SYNTHESE 5'-SUBSTITUIERTER ADENOSINDERIVATE [J].

JAHN, W .

CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (06) :1705-&

[10] 4'-SUBSTITUTED NUCLEOSIDES .2. SYNTHESIS OF NUCLEOSIDE ANTIBIOTIC NUCLEOCIDIN [J].

JENKINS, ID ;

VERHEYDEN, JPH ;

MOFFATT, JG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (11) :3346-3357

← 1 2 3 →