Details
| Original language | English |
|---|---|
| Pages (from-to) | 1228-1232 |
| Number of pages | 5 |
| Journal | Journal of Organic Chemistry |
| Volume | 60 |
| Issue number | 5 |
| Publication status | Published - 1 Mar 1995 |
| Externally published | Yes |
Abstract
A new application of organoiodine(III) is presented. Fully protected glycals are directly converted into 2, 3-dihydro-4H-pyran-4-ones by [hydroxyltosyloxy)iodo]benzene (Phl(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-4if-pyran-4-ones in yields up to 74%. In contrast, 4, 6-di-O-acetyl-3-deoxyglucal Polycoordinated Iodine.
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Journal of Organic Chemistry, Vol. 60, No. 5, 01.03.1995, p. 1228-1232.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Oxidation of Fully Protected Glycate by Hypervalent Iodine Reagents
AU - Kirschning, Andreas
PY - 1995/3/1
Y1 - 1995/3/1
N2 - A new application of organoiodine(III) is presented. Fully protected glycals are directly converted into 2, 3-dihydro-4H-pyran-4-ones by [hydroxyltosyloxy)iodo]benzene (Phl(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-4if-pyran-4-ones in yields up to 74%. In contrast, 4, 6-di-O-acetyl-3-deoxyglucal Polycoordinated Iodine.
AB - A new application of organoiodine(III) is presented. Fully protected glycals are directly converted into 2, 3-dihydro-4H-pyran-4-ones by [hydroxyltosyloxy)iodo]benzene (Phl(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-4if-pyran-4-ones in yields up to 74%. In contrast, 4, 6-di-O-acetyl-3-deoxyglucal Polycoordinated Iodine.
UR - http://www.scopus.com/inward/record.url?scp=0001527970&partnerID=8YFLogxK
U2 - 10.1021/jo00110a028
DO - 10.1021/jo00110a028
M3 - Article
AN - SCOPUS:0001527970
VL - 60
SP - 1228
EP - 1232
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 5
ER -