SYNTHESIS OF 2'-DEOXY-PYRANOSYL NUCLEOSIDES FROM GLYCALS THROUGH CONSECUTIVE ADDITION OF PHENYLSELENENYL CHLORIDE AND GLYCOSYLATION - A STUDY OF FACTORS CONTROLLING THE STEREOSELECTIVITY

被引：15

作者：

ELLAGHDACH, A ^{[1
]}

MATHEU, I ^{[1
]}

CASTILLON, S ^{[1
]}

机构：

[1] UNIV ROVIRA VIRGILI,DEPT QUIM,E-43005 TARRAGONA,SPAIN

来源：

TETRAHEDRON | 1994年 / 50卷 / 42期

关键词：

D O I：

10.1016/S0040-4020(01)89572-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2'-Deoxy-2'-phenylselenenyl-pyranosyl nucleosides have been synthesised in a stereoselective way starting from glycals using selenium reagents, and converted into 2'-deoxynucleosides by treatment with tributyltin hydride. The stereoselectivity of the reaction has been shown to be dependent on the protecting groups, the structure of the starting glycal, the phenylselenenyl reagent and the solvent. Nucleosides of beta-gluco beta-galacto and alpha-arabino configuration are principally obtained, starting from the corresponding benzyl protected glycals, using PhSeCl as an activating reagent and ehter as the solvent.

引用

页码：12219 / 12234

页数：16

共 43 条

[1] SYNTHESIS OF 2,4-DIDEOXY-BETA-D-ERYTHRO-HEXOPYRANOSYL NUCLEOSIDES
AUGUSTYNS, K
ROZENSKI, J
VANAERSCHOT, A
JANSSEN, G
HERDEWIJN, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) : 2977 - 2982
[2] SNCL4 VERSUS TICL4-MEDIATED COUPLING BETWEEN N-6-BENZOYLADENINE AND PERBENZOYLATED 2-DEOXYPYRANOSE - APPLICATION TO THE SYNTHESIS OF CERTAIN HOMOCHIRAL ACYCLONUCLEOSIDES AND CARBOACYCLONUCLEOSIDES
BAUD, MV
CHAVIS, C
LUCAS, M
IMBACH, JL
[J]. TETRAHEDRON, 1991, 47 (48) : 9993 - 10002
[3] BEAU JM, 1989, TETRAHEDRON LETT, V30, P75
[4] SYNTHESIS OF UNSATURATED 4'-AZIDO PYRANOSYL THYMINES AS POTENTIAL ANTIVIRAL AND ANTI-HIV AGENTS
BESSODES, M
EGRON, MJ
FILIPPI, J
ANTONAKIS, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11): : 3035 - 3039
[5] PALLADIUM(0)-BASED APPROACH TO HETEROCYCLIC N-GLYCOSYL DERIVATIVES
BOLITT, V
CHAGUIR, B
SINOU, D
[J]. TETRAHEDRON LETTERS, 1992, 33 (18) : 2481 - 2484
[6] BOWLES WA, 1964, J AM CHEM SOC, V86, P1256
[7] Broder S, 1987, AIDS MODERN CONCEPTS
[8] DeClercq E., 1990, DESIGN ANTIAIDS DRUG
[9] HETEROCYCLIC N-GLYCOSYL DERIVATIVES .19. GLYCAL NUCLEOSIDES - THEIR RELATIONSHIP WITH 2',3'-UNSATURATED NUCLEOSIDES AND THEIR UTILIZATION IN SYNTHESIS OF 1',3'-2 BASE NUCLEOSIDES
DELASHERAS, FG
STUD, M
[J]. TETRAHEDRON, 1977, 33 (12) : 1513 - 1518
[10] UNSATURATED CARBOHYDRATES .15. SYNTHESIS OF (3'-DEOXYHEX-2'-ENOPYRANOSYL)PURINE DERIVATIVES
FERRIER, RJ
PONPIPOM, MM
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (03): : 560 - &

← 1 2 3 4 5 →