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Titolo:
PREPARATION OF OPTICALLY-ACTIVE SUCCINIC ACID-DERIVATIVES - II - EFFICIENT AND PRACTICAL SYNTHESIS OF KAD-1229
Autore:
YAMAGUCHI T; YANAGI T; HOKARI H; MUKAIYAMA Y; KAMIJO T; YAMAMOTO I;
Indirizzi:
KISSEI PHARMACEUT CO LTD,CENT RES LABS,4365-1 KASHIWABARA NAGANO 39983 JAPAN KISSEI PHARMACEUT CO LTD,CENT RES LABS NAGANO 39983 JAPAN SHINSHU UNIV NAGANO 386 JAPAN
Titolo Testata:
Chemical and Pharmaceutical Bulletin
fascicolo: 2, volume: 46, anno: 1998,
pagine: 337 - 340
SICI:
0009-2363(1998)46:2<337:POOSA->2.0.ZU;2-T
Fonte:
ISI
Lingua:
ENG
Soggetto:
SULFONYLUREA HYPOGLYCEMIC AGENT; PROCHIRAL CARBOXYLIC-ACIDS; DIABETES-MELLITUS RATS; ASYMMETRIC HYDROGENATION; DIHYDRATE KAD-1229; COMPLEX; (S)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL;
Keywords:
KAD-1229; POTENT HYPOGLYCEMIC EFFECT; (S)-2-BENZYLSUCCINIC ACID; -3-(CIS-HEXAHYDROISOINDOLIN-2-YLCARBONYL)PROPIONIC ACID;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
17
Recensione:
Indirizzi per estratti:
Citazione:
T. Yamaguchi et al., "PREPARATION OF OPTICALLY-ACTIVE SUCCINIC ACID-DERIVATIVES - II - EFFICIENT AND PRACTICAL SYNTHESIS OF KAD-1229", Chemical and Pharmaceutical Bulletin, 46(2), 1998, pp. 337-340

Abstract

For large-scale synthesis of monocalcium ahydroisoindolin-2-ylcarbonyl)propionate]dihydrate (1, KAD-1229), we investigated regioselective reactions of (S)-2-benzylsuccinic acid (2),vith cis-hexahydroisoindoline (4). It was difficult to obtain a half amide regioselectively through coupling reaction of the (S)-acid 2 with the amine 4. Therefore, thesuccinic acid 2 was converted to his-activated esters 3a-c and these were reacted with 4 to give the amides 5a-c in good yields, regioselectively. The amides 5a-c were derived to KAD-1229, which has a potent hypoglycemic effect, in good yields.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 25/11/20 alle ore 04:37:44