Details
| Original language | English |
|---|---|
| Pages (from-to) | 2267-2274 |
| Number of pages | 8 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 11 |
| Publication status | Published - Nov 1998 |
| Externally published | Yes |
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.
Keywords
- Carbohydrates, Glycals, Glycosylation, Hypervalent iodine
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, No. 11, 11.1998, p. 2267-2274.
Research output: Contribution to journal › Review article › Research › 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 -