L-ASPARTIC ACID BIS(TRIMETHYLSILYL) ESTER - A CONVENIENT STARTING MATERIAL FOR THE ACYLATION OF L-ASPARTIC ACID

被引：6

作者：

CASTANO, AM ^{[1
]}

ECHAVARREN, AM ^{[1
]}

机构：

[1] CSIC,INST QUIM ORGAN,JUAN DE LA CIERVA 3,E-28006 MADRID,SPAIN

来源：

TETRAHEDRON | 1992年 / 48卷 / 16期

关键词：

ASPARTIC ACID; SILYLATION; ACYLATION; MTPA-ASPARTIC ACID; DIPEPTIDES;

D O I：

10.1016/0040-4020(92)85013-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Reaction of L-aspartic acid with excess of bis(trimethylsilyl)amine under reflux provides optically pure L-aspartic acid bis(trimethylsilyl) ester in quantitative yield. This silyl ester reacts with a variety of acylating reagents in tetrahydrofuran to give N-protected aspartic acids and dipeptides in good yields without racemization.

引用

页码：3377 / 3384

页数：8

共 36 条

[1]

ANTEUNIS MJO, 1990, B SOC CHIM BELG, V99, P361

[2]

EFFICIENT ONE-POT SYNTHESIS OF N-TRITYL AMINO-ACIDS [J].

BARLOS, K ;

PAPAIOANNOU, D ;

THEODOROPOULOS, D .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1324-1326

[3]

BECU C, 1990, B SOC CHIM BELG, V99, P779

[4]

AMINO-ACID FLUORIDES - THEIR PREPARATION AND USE IN PEPTIDE-SYNTHESIS [J].

BERTHO, JN ;

LOFFET, A ;

PINEL, C ;

REUTHER, F ;

SENNYEY, G .

TETRAHEDRON LETTERS, 1991, 32 (10) :1303-1306

[5]

CATALYSTS FOR SILYLATIONS WITH 1,1,1,3,3,3-HEXAMETHYLDISILAZANE [J].

BRUYNES, CA ;

JURRIENS, TK .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3966-3969

[6]

ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - AMINO ACYLATION WITH N-ACYLAMINO ACIDS [J].

BUCKLEY, TF ;

RAPOPORT, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6157-6163

[7]

((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID FLUORIDES - CONVENIENT NEW PEPTIDE COUPLING REAGENTS APPLICABLE TO THE FMOC/TERT-BUTYL STRATEGY FOR SOLUTION AND SOLID-PHASE SYNTHESES [J].

CARPINO, LA ;

SADATAALAEE, D ;

CHAO, HG ;

DESELMS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9651-9652

[8]

((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID CHLORIDES - SYNTHESIS, CHARACTERIZATION, AND APPLICATION TO THE RAPID SYNTHESIS OF SHORT PEPTIDE SEGMENTS [J].

CARPINO, LA ;

COHEN, BJ ;

STEPHENS, KE ;

SADATAALAEE, SY ;

TIEN, JH ;

LANGRIDGE, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3732-3734

[9]

TERT-BUTYLOXYCARBONYL AND BENZYLOXYCARBONYL AMINO-ACID FLUORIDES - NEW, STABLE RAPID-ACTING ACYLATING AGENTS FOR PEPTIDE-SYNTHESIS [J].

CARPINO, LA ;

MANSOUR, EME ;

SADATAALAEE, D .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2611-2614

[10]

CARSON JF, 1981, SYNTHESIS-STUTTGART, P268

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