New family of base- and nucleophile-sensitive amino-protecting groups. A Michael-acceptor-based deblocking process. Practical utilization of the 1,1-dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) group

被引：37

作者：

Carpino, LA

Philbin, M

Ismail, M

Truran, GA

Mansour, EME

Iguchi, S

Ionescu, D

El-Faham, A

Riemer, C

Warrass, R

Weiss, MS

机构：

[1] Department of Chemistry, University of Massachusetts, Amherst

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1997年 / 119卷 / 41期

关键词：

D O I：

10.1021/ja9713690

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

[No abstract available]

引用

页码：9915 / 9916

页数：2

共 12 条

[1] SIDE REACTIONS IN PEPTIDE-SYNTHESIS .11. POSSIBLE REMOVAL OF THE 9-FLUORENYLMETHYLOXYCARBONYL GROUP BY THE AMINO COMPONENTS DURING COUPLING [J].

BODANSZKY, M ;

DESHMANE, SS ;

MARTINEZ, J .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1622-1625

[2] THE ((BETA-PHENYLETHYL)OXY)CARBONYL(HOMOBENZYLOXYCARBONYL,HZ) AMINO-PROTECTING GROUP [J].

CARPINO, LA ;

TUNGA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1930-1932

[3] Peptide synthesis via amino acid halides [J].

Carpino, LA ;

Beyermann, M ;

Wenschuh, H ;

Bienert, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) :268-274

[4] EFFICIENCY IN PEPTIDE COUPLING - 1-HYDROXY-7-AZABENZOTRIAZOLE VS 3,4-DIHYDRO-3-HYDROXY-4-OXO-1,2,3-BENZOTRIAZINE [J].

CARPINO, LA ;

EL-FAHAM, A ;

ALBERICIO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3561-3564

[5] ADVANTAGEOUS APPLICATIONS OF AZABENZOTRIAZOLE (TRIAZOLOPYRIDINE)-BASED COUPLING REAGENTS TO SOLID-PHASE PEPTIDE-SYNTHESIS [J].

CARPINO, LA ;

EL-FAHAM, A ;

MINOR, CA ;

ALBERICIO, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) :201-203

[6] THE 2-CHLORO-3-INDENYLMETHYLOXYCARBONYL AND BENZ[F]INDEN-3-YLMETHYLOXYCARBONYL BASE-SENSITIVE AMINO-PROTECTING GROUPS - APPLICATION TO AN INVERSE MERRIFIELD APPROACH TO PEPTIDE-SYNTHESIS [J].

CARPINO, LA ;

COHEN, BJ ;

LIN, YZ ;

STEPHENS, KE ;

TRIOLO, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :251-259

[7] NOVEL CARBOXYLIC-ACID AND CARBOXAMIDE PROTECTIVE GROUPS BASED ON THE EXCEPTIONAL STABILIZATION OF THE CYCLOPROPYLMETHYL CATION [J].

CARPINO, LA ;

CHAO, HG ;

GHASSEMI, S ;

MANSOUR, EME ;

RIEMER, C ;

WARRASS, R ;

SADATAALAEE, D ;

TRURAN, GA ;

IMAZUMI, H ;

EL-FAHAM, A ;

IONESCU, D ;

ISMAIL, M ;

KOWALESKI, TL ;

HAN, CH ;

WENSCHUH, H ;

BEYERMANN, M ;

BIENERT, M ;

SHROFF, H ;

ALBERICIO, F ;

TRIOLO, SA ;

SOLE, NA ;

KATES, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :7718-7719

[8] AN EXTREMELY MILD METHOD FOR THE CONVERSION OF A PRIMARY ALKYL HALIDE INTO A PRIMARY ALCOHOL [J].

HARRIS, M ;

BULL, MJ .

SYNTHETIC COMMUNICATIONS, 1985, 15 (14) :1225-1228

[9] 3-BROMO-2-(TERT-BUTYLSULFONYL)-1-PROPENE - A MULTI-COUPLING REAGENT .1. [J].

KNOCHEL, P ;

NORMANT, JF .

TETRAHEDRON LETTERS, 1985, 26 (04) :425-428

[10]

Lauer J.L., 1995, LETT PEPT SCI, V1, P197, DOI [DOI 10.1007/BF00117955, 10.1007/BF00117955]

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