SYNTHESIS AND SELECTIVE DEPROTECTION OF THE PENTA-N-PROTECTED POLYAMINE 1,16-DIAMINO-4,8,13-TRIAZAHEXADECANE

被引：19

作者：

GOULAOUICDUBOIS, C ^{[1
]}

GUGGISBERG, A ^{[1
]}

HESSE, M ^{[1
]}

机构：

[1] UNIV ZURICH,INST ORGAN CHEM,CH-8057 ZURICH,SWITZERLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 46期

关键词：

D O I：

10.1016/0040-4020(95)00811-L

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the penta-N-protected polyamine thermopentamine {PA 3343, 1a, tert-butyl N-[4-benzyl-16-diallylamino-13-(pyridine-2-sulfonyl)-9-trifluoroacetyl-4,9,13-triazahexadec-1-yl]-carbamate}, containing five different N-protecting groups is described. These protecting groups include tert-butoxycarbonyl, benzyl, trifluoroacetyl, diallyl, and pyridine-2-sulfonyl. In spite of the syntheses of specific polyamine derivatives the selective removal of each of these groups has been investigated.

引用

页码：12573 / 12582

页数：10

共 27 条

[1] POTASSIUM FLUORIDE ON CELITE - VERSATILE REAGENT FOR C-ALKYLATION,N-ALKYLATION,O-ALKYLATION, AND S-ALKYLATION [J].

ANDO, T ;

YAMAWAKI, J .

CHEMISTRY LETTERS, 1979, (01) :45-46

[2]

[Anonymous], EXCITATORY AMINO ACI

[3] NEW AMINO PROTECTING GROUP REMOVABLE BY REDUCTION - CHEMISTRY OF DITHIASUCCINOYL (DTS) FUNCTION [J].

BARANY, G ;

MERRIFIELD, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (22) :7363-7365

[4] REAGENTS FOR THE STEPWISE FUNCTIONALIZATION OF SPERMIDINE, HOMOSPERMIDINE, AND BIS(3-AMINOPROPYL)AMINE [J].

BERGERON, RJ ;

GARLICH, JR ;

STOLOWICH, NJ .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) :2997-3001

[5] REAGENTS FOR THE STEPWISE FUNCTIONALIZATION OF SPERMINE [J].

BERGERON, RJ ;

MCMANIS, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) :3108-3111

[6] STRUCTURAL REQUIREMENTS FOR THE DEVELOPMENT OF POTENT N-METHYL-D-ASPARTIC ACID (NMDA) RECEPTOR ANTAGONISTS [J].

BIGGE, CF .

BIOCHEMICAL PHARMACOLOGY, 1993, 45 (08) :1547-1561

[7] PREPARATION OF DIAMINO ETHERS AND POLYAMINES [J].

BRADSHAW, JS ;

KRAKOWIAK, KE ;

IZATT, RM .

TETRAHEDRON, 1992, 48 (22) :4475-4515

[8]

COREY EJ, 1975, SYNTHESIS-STUTTGART, P590

[9] SYNTHESIS OF SELECTIVELY N-FUNCTIONALIZED POLYAMINE DERIVATIVES [J].

FIEDLER, WJ ;

HESSE, M .

HELVETICA CHIMICA ACTA, 1993, 76 (04) :1511-1519

[10]

FIEDLER WJ, 1993, HELV CHIM ACTA, V76, P11667

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