OXIDATION OF FULLY PROTECTED GLYCALS BY HYPERVALENT IODINE REAGENTS

被引：57

作者：

KIRSCHNING, A

机构：

[1] Institut für Organische Chemie der Technischen Universitat Clausthal, Clausthal-Zellerfeld, Leibnizstrasse 6

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 05期

关键词：

D O I：

10.1021/jo00110a028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new application of organoiodine(III) is presented. Fully protected glycals are directly converted into 2,3-dihydro-4H-pyran-4-ones by [hydroxy(tosyloxy)iodo]benzene (PhI(OH)OTs, 1). The detailed study reveals that this conversion is independent of the relative stereochemistry as well as the nature of protection on the pyran ring. 3-O-Silyl groups are most smoothly converted into the keto group giving 2,3-dihydro-4H-pyran-4-ones in yields up to 74%. In contrast, 4,6-di-O-acetyl-3-deoxyglucal (19) affords the rearranged oxidation product 32. Both observations can be reconciled by the proposed mechanism.

引用

页码：1228 / 1232

页数：5

共 60 条

[1] C-GLYCOSYL COMPOUNDS .4. SYNTHESIS OF (2-DEOXY-ALPHA-D-GLYC-2-ENOPYRANOSYL)ARENES BY STEREOSPECIFIC CONJUGATE-ADDITION OF ORGANOCOPPER REAGENTS TO PERACETYLATED HEX-1-ENOPYRAN-3-ULOSES [J].

BELLOSTA, V ;

CZERNECKI, S .

CARBOHYDRATE RESEARCH, 1987, 171 :279-288

[2]

BELLOSTA V, 1993, SYNLETT, P861

[3] PALLADIUM-MEDIATED ARYLATION OF ACETYLATED ENONES DERIVED FROM GLYCALS .4. SYNTHESIS OF ARYL 2-DEOXY-BETA-D-C-GLYCOPYRANOSIDES [J].

BENHADDOU, R ;

CZERNECKI, S ;

VILLE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4612-4616

[4] CONVENIENT PREPARATIONS OF 2,3-DIHYDRO-4H-PYRAN-4-ONES FROM D-GLUCAL TRIACETATE - SELECTIVE OXIDATIONS OF ALYLLIC ACETATES AND ALLYLIC SILYL ETHERS USING N-BROMOSUCCINIMIDE [J].

BOUILLOT, A ;

KHAC, DD ;

FETIZON, M ;

GUIR, F ;

MEMORIA, Y .

SYNTHETIC COMMUNICATIONS, 1993, 23 (15) :2071-2081

[5] THE EFFECT OF SUBSTITUENTS ON THE REACTIVITY OF THE DOUBLE-BOND OF D-GLYCALS [J].

BOVIN, NV ;

ZURABYAN, SE ;

KHORLIN, AY .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1983, 2 (03) :249-262

[6] APPLICATION OF THE IBUKA-YAMAMOTO REACTION TO A PROBLEM IN STEREOCHEMICAL COMMUNICATION - A STRATEGY FOR THE STEREOSPECIFIC SYNTHESIS AND STABILIZATION OF THE TRIENE SUBSTRUCTURE OF RAPAMYCIN THROUGH SULFONE SUBSTITUTION [J].

CHEN, SH ;

HORVATH, RF ;

JOGLAR, J ;

FISHER, MJ ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5834-5845

[7] AN IMPROVED SYNTHESIS AND NMR-SPECTRA OF BENZYLATED GLYCALS [J].

CHMIELEWSKI, M ;

FOKT, I ;

GRODNER, J ;

GRYNKIEWICZ, G ;

SZEJA, W .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (05) :735-741

[8] ACYLKETENE [4+2] CYCLOADDITIONS - DIVERGENT DENOVO SYNTHESIS OF 2,6-DIDEOXY SUGARS [J].

COLEMAN, RS ;

FRASER, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :385-392

[9] ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].

COREY, EJ ;

CYWIN, CL ;

ROPER, TD .

TETRAHEDRON LETTERS, 1992, 33 (46) :6907-6910

[10] AZIDO-PHENYLSELENYLATION OF PROTECTED GLYCALS [J].

CZERNECKI, S ;

RANDRIAMANDIMBY, D .

TETRAHEDRON LETTERS, 1993, 34 (49) :7915-7916

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