Reaction of 1,3-dimethyl-5-acetyl-barbituric acid (DAB) with primary amines. Access to intermediates for selectively protected spermidines

被引:14
作者
da Silva, ET [1 ]
Lima, ELS [1 ]
机构
[1] Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, BR-21945970 Rio De Janeiro, Brazil
关键词
D O I
10.1016/S0040-4039(03)00709-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
dThe ability of 1, 3 -dimethyl-5-acetyl-barbituric acid (DAB) to react with primary amines in a chemoselective fashion was applied to the synthesis of a selectively protected spermidine. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3621 / 3624
页数:4
相关论文
共 23 条
[1]  
ALMEIDA MV, 2000, J BRAZIL CHEM SOC, V11, P154
[2]   An efficient synthesis of orthogonally protected spermidine [J].
Amssoms, K ;
Augustyns, K ;
Yamani, A ;
Zhang, M ;
Haemers, A .
SYNTHETIC COMMUNICATIONS, 2002, 32 (03) :319-328
[3]   A new linker for primary amines applicable to combinatorial approaches. [J].
Bannwarth, W ;
Huebscher, J ;
Barner, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (13) :1525-1528
[4]   METHODS FOR THE SELECTIVE MODIFICATION OF SPERMIDINE AND ITS HOMOLOGS [J].
BERGERON, RJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (04) :105-113
[5]   PREPARATION OF DIAMINO ETHERS AND POLYAMINES [J].
BRADSHAW, JS ;
KRAKOWIAK, KE ;
IZATT, RM .
TETRAHEDRON, 1992, 48 (22) :4475-4515
[6]  
CARPINO LA, 1973, ORG SYNTH, V5, P157
[7]   A NOVEL 4-AMINOBENZYL ESTER-BASED CARBOXY-PROTECTING GROUP FOR SYNTHESIS OF ATYPICAL PEPTIDES BY FMOC-BU(T) SOLID-PHASE CHEMISTRY [J].
CHAN, WC ;
BYCROFT, BW ;
EVANS, DJ ;
WHITE, PD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (21) :2209-2210
[8]   A Dde-based carboxy linker for solid-phase synthesis [J].
Chhabra, SR ;
Parekh, H ;
Khan, AN ;
Bycroft, BW ;
Kellam, B .
TETRAHEDRON LETTERS, 2001, 42 (11) :2189-2192
[9]   An appraisal of new variants of Dde amine protecting group for solid phase peptide synthesis [J].
Chhabra, SR ;
Hothi, B ;
Evans, DJ ;
White, PD ;
Bycroft, BW ;
Chan, WC .
TETRAHEDRON LETTERS, 1998, 39 (12) :1603-1606
[10]   Solid-phase synthesis of symmetrical and unsymmetrical polyamine analogues of philanthotoxins using a Dde-linker [J].
Chhabra, SR ;
Khan, AN ;
Bycroft, BW .
TETRAHEDRON LETTERS, 2000, 41 (07) :1095-1098