Stereoselective synthesis of 2',3'-dideoxynucleosides by addition of selenium electrophiles to glycals. A formal synthesis of D4T from 2-deoxyribose

被引:46
作者
Diaz, Y [1 ]
ElLaghdach, A [1 ]
Matheu, MI [1 ]
Castillon, S [1 ]
机构
[1] UNIV ROVIRA & VIRGILI,DEPT QUIM,TARRAGONA 43005,SPAIN
关键词
D O I
10.1021/jo9616825
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[No abstract available]
引用
收藏
页码:1501 / 1505
页数:5
相关论文
共 32 条
  • [1] A HIGHLY STEREOSELECTIVE SYNTHESIS OF ANTI-HIV 2',3'-DIDEOXYNUCLEOSIDES AND 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES
    BEACH, JW
    KIM, HO
    JEONG, LS
    NAMPALLI, S
    ISLAM, Q
    AHN, SK
    BABU, JR
    CHU, CK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) : 3887 - 3894
  • [2] EFFICIENT TRANSFORMATION OF THYMIDINE INTO 2',3'-DIDEHYDRO-2',3'-DIDEOXY-THYMIDINE (D4T) INVOLVING OPENING OF A 2,3'-ANHYDRO DERIVATIVE BY PHENYLSELENOL
    BECOUARN, S
    CZERNECKI, S
    VALERY, JM
    [J]. NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (06): : 1227 - 1232
  • [3] Broder S, 1987, AIDS MODERN CONCEPTS
  • [4] A HIGHLY STEREOSELECTIVE GLYCOSYLATION OF 2-(PHENYLSELENENYL)-2,3-DIDEOXYRIBOSE DERIVATIVE WITH THYMINE - SYNTHESIS OF 3'-DEOXY-2',3'-DIDEHYDROTHYMIDINE AND 3'-DEOXYTHYMIDINE
    CHU, CK
    BABU, JR
    BEACH, JW
    AHN, SK
    HUANG, HQ
    JEONG, LS
    LEE, SJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) : 1418 - 1420
  • [5] DeClercq E., 1990, DESIGN ANTIAIDS DRUG
  • [6] DUEHOLM KL, 1992, SYNTHESIS-STUTTGART, P1
  • [7] SELENIUM-CONTROLLED STEREOSELECTIVE SYNTHESIS OF 2'-DEOXYNUCLEOSIDES FROM GLYCALS - A FORMAL SYNTHESIS OF AZT
    ELLAGHDACH, A
    DIAZ, Y
    CASTILLON, S
    [J]. TETRAHEDRON LETTERS, 1993, 34 (17) : 2821 - 2822
  • [8] SYNTHESIS OF 2'-DEOXY-PYRANOSYL NUCLEOSIDES FROM GLYCALS THROUGH CONSECUTIVE ADDITION OF PHENYLSELENENYL CHLORIDE AND GLYCOSYLATION - A STUDY OF FACTORS CONTROLLING THE STEREOSELECTIVITY
    ELLAGHDACH, A
    MATHEU, I
    CASTILLON, S
    [J]. TETRAHEDRON, 1994, 50 (42) : 12219 - 12234
  • [9] A SIMPLE SYNTHETIC ROUTE TO SILYLATED METHYL 3-AZIDO-2,3-DIDEOXY-ALPHA,BETA-D-ERYTHRO-PENTOFURANOSIDE
    HANSEN, P
    PEDERSEN, EB
    [J]. ACTA CHEMICA SCANDINAVICA, 1990, 44 (05): : 522 - 523
  • [10] JAURAND G, 1981, J CHEM SOC CHEM COMM, P527