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Titolo:
DOUBLE DIASTEREOSELECTIVE GLUCOSIDATION OF CYCLIC HEMIACETALS - SYNTHESIS OF THE 1,4-BENZOXAZINONE ACETAL GLUCOSIDES GDIBOA AND GDIMBOA FROM GRAMINEAE
Autore:
KLUGE M; SICKER D;
Indirizzi:
UNIV LEIPZIG,INST ORGAN CHEM,TALSTR 35 D-04103 LEIPZIG GERMANY UNIV LEIPZIG,INST ORGAN CHEM D-04103 LEIPZIG GERMANY
Titolo Testata:
Tetrahedron
fascicolo: 31, volume: 52, anno: 1996,
pagine: 10389 - 10398
SICI:
0040-4020(1996)52:31<10389:DDGOCH>2.0.ZU;2-0
Fonte:
ISI
Lingua:
ENG
Soggetto:
HYDROXAMIC ACIDS; STEREOSELECTIVE SYNTHESIS; IRIDOIDS; BENZOXAZOLINONE; ALLELOCHEMICALS; IDENTIFICATION; RESISTANCE; GLYCOSIDES; EXTRACTS; SKELETON;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
43
Recensione:
Indirizzi per estratti:
Citazione:
M. Kluge e D. Sicker, "DOUBLE DIASTEREOSELECTIVE GLUCOSIDATION OF CYCLIC HEMIACETALS - SYNTHESIS OF THE 1,4-BENZOXAZINONE ACETAL GLUCOSIDES GDIBOA AND GDIMBOA FROM GRAMINEAE", Tetrahedron, 52(31), 1996, pp. 10389-10398

Abstract

A double diastereoselective glucosidation procedure giving rise in one step to the natural (2R)-2-beta-configuration of 6 and for the firsttime, 7, benzoxazinoid acetal glucosides from Gramineae species, is described by reaction of O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl) trichloroacetimidate 3 as glucosyl donor with 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one 1 or its 7-methoxy derivative 2 as hemiacetalic glucosyl accepters in the presence of excess borontrifluoride etherate as promoter without a need for a covalent protection of the cyclic hydroxamic acid unit in the aglucones. Copyright (C) 1996 Elsevier Science Ltd

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Documento generato il 03/07/20 alle ore 22:40:29