Synthesis of acyclic nucleotide analogues derived from N-substituted 6-(1-aminoethyl)purines via 6-acetylpurine derivatives

被引：34

作者：

Hocek, M

Masojidkova, M

Holy, A

机构：

[1] Inst. of Organ. Chem. and Biochem., Acad. of Sci. of the Czech Republic

来源：

TETRAHEDRON | 1997年 / 53卷 / 06期

关键词：

D O I：

10.1016/S0040-4020(96)01130-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Stille coupling of 9-{2-[bis(2-propoxy)phosphonylmethoxy]ethyl}-6-chloropurines with 1-(ethoxyvinyl)tributyltin afforded 6-(1-ethoxyvinyl)purine derivatives. Their acid hydrolysis gave 6-acetylpurine derivatives that after reductive amination using various primary and secondary amine hydrochlorides and sodium cyanoborohydride followed by deprotection afforded the title N-substituted 6-(1-aminoethyl)-9-(2-phosphonomethoxyethyl)purine derivatives. (C) 1997, Elsevier Science Ltd.

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页码：2291 / 2302

页数：12

相关论文

共 26 条

[1]

ANDREI G, UNPUB

[2]

[Anonymous], [No title captured]

[3] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].

BORCH, RF ;

BERNSTEIN, MD ;

DURST, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+

[4] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].

CABRI, W ;

CANDIANI, I .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7

[5] 6-CHLOROPURINES AND ORGANOSTANNANES IN PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS [J].

GUNDERSEN, LL .

TETRAHEDRON LETTERS, 1994, 35 (19) :3155-3158

[6] 6-HALOPURINES IN PALLADIUM-CATALYZED COUPLING WITH ORGANOTIN AND ORGANOZINC REAGENTS [J].

GUNDERSEN, LL ;

BAKKESTUEN, AK ;

AASEN, AJ ;

OVERAS, H ;

RISE, F .

TETRAHEDRON, 1994, 50 (32) :9743-9756

[7]

HIGASHINO T, 1982, CHEM PHARM BULL, V30, P4521

[8] Synthesis and antiviral activity of acyclic nucleotide analogues derived from 6-(aminomethyl)purines and purine-6-carboxamidines [J].

Hocek, M ;

Masojidkova, M ;

Holy, A ;

Andrei, G ;

Snoeck, R ;

Balzarini, J ;

DeClercq, E .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1996, 61 (10) :1525-1537

[9] A FACILE SYNTHESIS OF 6-CYANOPURINE BASES [J].

HOCEK, M ;

HOLY, A .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1995, 60 (08) :1386-1389

[10] SYNTHESIS OF ACYCLIC NUCLEOTIDE ANALOGS DERIVED FROM 2-(AMINOMETHYL)ADENINE AND 2-(AMINOMETHYL)HYPOXANTHINE [J].

HOCEK, M ;

MASOJIDKOVA, M ;

HOLY, A .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1995, 60 (05) :875-882