Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 2267-2274 |
| Seitenumfang | 8 |
| Fachzeitschrift | European Journal of Organic Chemistry |
| Ausgabenummer | 11 |
| Publikationsstatus | Veröffentlicht - Nov. 1998 |
| Extern publiziert | Ja |
Abstract
Synthetic applications of hypervalent iodine reagents in the oxidation state +3 in relation to unsaturated carbohydrates are reviewed. By using the Koser reagent or its bis(azido) derivative, fully protected glycals are oxidatively deblocked in the allylic position. The reaction furnishes carbohydrate-derived 2,3-dihydro-4H-pyranones, which serve as starting materials for the preparation of C-saccharides, glycosyl stannanes or thromboxane A2-analogues. Alternatively, iodine(III) reagents can be used to oxidize halide anions. The halogen-ate complexes thus generated behave like synthetic equivalents of acyl hypobromite and iodite, respectively, or halogen azides, which can all add to alkenes, including glycals, under very mild conditions.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Physikalische und Theoretische Chemie
- Chemie (insg.)
- Organische Chemie
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in: European Journal of Organic Chemistry, Nr. 11, 11.1998, S. 2267-2274.
Publikation: Beitrag in Fachzeitschrift › Übersichtsarbeit › Forschung › Peer-Review
}
TY - JOUR
T1 - Hypervalent iodine and carbohydrates
T2 - A new liaison
AU - Kirschning, Andreas
PY - 1998/11
Y1 - 1998/11
N2 - Synthetic applications of hypervalent iodine reagents in the oxidation state +3 in relation to unsaturated carbohydrates are reviewed. By using the Koser reagent or its bis(azido) derivative, fully protected glycals are oxidatively deblocked in the allylic position. The reaction furnishes carbohydrate-derived 2,3-dihydro-4H-pyranones, which serve as starting materials for the preparation of C-saccharides, glycosyl stannanes or thromboxane A2-analogues. Alternatively, iodine(III) reagents can be used to oxidize halide anions. The halogen-ate complexes thus generated behave like synthetic equivalents of acyl hypobromite and iodite, respectively, or halogen azides, which can all add to alkenes, including glycals, under very mild conditions.
AB - Synthetic applications of hypervalent iodine reagents in the oxidation state +3 in relation to unsaturated carbohydrates are reviewed. By using the Koser reagent or its bis(azido) derivative, fully protected glycals are oxidatively deblocked in the allylic position. The reaction furnishes carbohydrate-derived 2,3-dihydro-4H-pyranones, which serve as starting materials for the preparation of C-saccharides, glycosyl stannanes or thromboxane A2-analogues. Alternatively, iodine(III) reagents can be used to oxidize halide anions. The halogen-ate complexes thus generated behave like synthetic equivalents of acyl hypobromite and iodite, respectively, or halogen azides, which can all add to alkenes, including glycals, under very mild conditions.
KW - Carbohydrates
KW - Glycals
KW - Glycosylation
KW - Hypervalent iodine
UR - http://www.scopus.com/inward/record.url?scp=2842528404&partnerID=8YFLogxK
U2 - 10.1002/(sici)1099-0690(199811)1998:11<2267::aid-ejoc2267>3.0.co;2-e
DO - 10.1002/(sici)1099-0690(199811)1998:11<2267::aid-ejoc2267>3.0.co;2-e
M3 - Review article
AN - SCOPUS:2842528404
SP - 2267
EP - 2274
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 11
ER -