7-SUBSTITUTED 7-DEAZA-2'-DEOXYGUANOSINES - REGIOSELECTIVE HALOGENATION OF PYRROLO[2,3-D]PYRIMIDINE NUCLEOSIDES

被引：50

作者：

RAMZAEVA, N ^{[1
]}

SEELA, F ^{[1
]}

机构：

[1] UNIV OSNABRUCK,INST CHEM,ORGAN & BIOORGAN CHEM LAB,D-49076 OSNABRUCK,GERMANY

来源：

HELVETICA CHIMICA ACTA | 1995年 / 78卷 / 05期

关键词：

D O I：

10.1002/hlca.19950780505

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of 7-chloro-, 7-bromo-, and 7-iodo-substituted 7-deaza-2'-deoxyguanosine derivatives 2b-d is described. The regioselective 7-halogenation with N-halogenosuccinimides was accomplished using 7-[2-deoxy-3,5- O-di(2-methylpropanoyl)-beta-D-erytilro-pentofuranosyl]-2-(formylamino)-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine (4) as the common precursor. A one-pot reaction (2N aq. NaOH) of the halogenated intermediates 5a-c furnished the desired compounds. Also the 7-hexynyl derivative 2e of 7-deaza-2'-deoxyguanosine is described.

引用

页码：1083 / 1090

页数：8

共 29 条

[1] PYRROLOPYRIMIDINE NUCLEOSIDES .19. A TOTAL SYNTHESIS OF THE NUCLEOSIDE ANTIBIOTIC CADEGUOMYCIN [2-AMINO-7-(BETA-D-RIBOFURANOSYL)-PYRROLO[2,3-D]PYRIMIDIN-4-ONE-5-CARBOXYLIC ACID] [J].

BEYLIN, VG ;

KAWASAKI, AM ;

CHENG, CS ;

TOWNSEND, LB .

TETRAHEDRON LETTERS, 1983, 24 (44) :4793-4796

[2] TOTAL SYNTHESIS OF 7-IODO-2',3'-DIDEOXY-7-DEAZAPURINE NUCLEOSIDES, KEY INTERMEDIATES IN THE PREPARATION OF REAGENTS FOR THE AUTOMATED SEQUENCING OF DNA [J].

COCUZZA, AJ .

TETRAHEDRON LETTERS, 1988, 29 (33) :4061-4064

[3] NUCLEOTIDE SEQUENCE OF ESCHERICHIA COLI TYROSIE TRANSFER RIBONUCLEIC ACID [J].

DOCTOR, BP ;

LOEBEL, JE ;

SODD, MA ;

WINTER, DB .

SCIENCE, 1969, 163 (3868) :693-&

[4] AMBER SUPPRESSION - A NUCLEOTIDE CHANGE IN ANTICODON OF A TYROSINE TRANSFER RNA [J].

GOODMAN, HM ;

ABELSON, J ;

LANDY, A ;

BRENNER, S ;

SMITH, JD .

NATURE, 1968, 217 (5133) :1019-&

[5]

GREGSON JM, 1993, J BIOL CHEM, V268, P10076

[6] PALLADIUM-CATALYZED SYNTHESIS OF ALKYNYLAMINO NUCLEOSIDES - A UNIVERSAL LINKER FOR NUCLEIC-ACIDS [J].

HOBBS, FW .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) :3420-3422

[7] STRUCTURE OF MODIFIED NUCLEOSIDE-Q ISOLATED FROM ESCHERICHIA-COLI TRANSFER RIBONUCLEIC-ACID - 7-(4,5-CIS-DIHYDROXY-1-CYCLOPENTEN-3-YLAMINOMETHYL)-7-DEAZAGUANOSINE [J].

KASAI, H ;

OHASHI, Z ;

HARADA, F ;

NISHIMURA, S ;

OPPENHEIMER, NJ ;

CRAIN, PF ;

LIEHR, JG ;

MINDEN, DLV ;

MCCLOSKEY, JA .

BIOCHEMISTRY, 1975, 14 (19) :4198-4208

[8] SYNTHESIS OF CADEGUOMYCIN (7-DEAZAGUANOSINE-7-CARBOXYLIC ACID) [J].

KONDO, T ;

GOTO, T ;

OKABE, T ;

TANAKA, N .

TETRAHEDRON LETTERS, 1983, 24 (34) :3647-3650

[9] SYNTHESES OF HYPERMODIFIED NUCLEOSIDE-Q, AND ITS BIOSYNTHETIC PRECURSORS PREQ0 AND PREQ1 [J].

KONDO, T ;

OKAMOTO, K ;

OHGI, T ;

GOTO, T .

TETRAHEDRON, 1986, 42 (01) :207-213

[10] A TOTAL SYNTHESIS OF CADEGUOMYCIN, A NUCLEOSIDE ANTIBIOTIC PRODUCED BY STREPTOMYCES HYGROSCOPICUS [J].

KONDO, T ;

OKAMOTO, K ;

YAMAMOTO, M ;

GOTO, T ;

TANAKA, N .

TETRAHEDRON, 1986, 42 (01) :199-205

← 1 2 3 →