Details
| Original language | English |
|---|---|
| Pages (from-to) | 8999-9002 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 40 |
| Issue number | 51 |
| Publication status | Published - 17 Dec 1999 |
| Externally published | Yes |
Abstract
Polymer-supported electrophilic reagents are prepared which efficiently add to carbohydrate-derived glycals under very mild conditions. Depending on the hypervalent reagent initially employed for oxidizing polymer-bound halides 1a or 1b both acetoxyhalogenations or azidoiodination can be carried out. With sugar-derived glycals, 2-deoxy-2-halo-pyranosyl acetates or azides are generated in excellent yield. Free hydroxy groups are tolerated. Even, fully unprotected glucal 23 can be employed for the short synthesis of 2-deoxy-2-iodo glycosyl acetates 24a,b.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Organic Chemistry
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In: Tetrahedron Letters, Vol. 40, No. 51, 17.12.1999, p. 8999-9002.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Application of polymer-supported electrophilic reagents for the 1,2-functionalization of glycals
AU - Kirschning, Andreas
AU - Jesberger, Martin
AU - Monenschein, Holger
PY - 1999/12/17
Y1 - 1999/12/17
N2 - Polymer-supported electrophilic reagents are prepared which efficiently add to carbohydrate-derived glycals under very mild conditions. Depending on the hypervalent reagent initially employed for oxidizing polymer-bound halides 1a or 1b both acetoxyhalogenations or azidoiodination can be carried out. With sugar-derived glycals, 2-deoxy-2-halo-pyranosyl acetates or azides are generated in excellent yield. Free hydroxy groups are tolerated. Even, fully unprotected glucal 23 can be employed for the short synthesis of 2-deoxy-2-iodo glycosyl acetates 24a,b.
AB - Polymer-supported electrophilic reagents are prepared which efficiently add to carbohydrate-derived glycals under very mild conditions. Depending on the hypervalent reagent initially employed for oxidizing polymer-bound halides 1a or 1b both acetoxyhalogenations or azidoiodination can be carried out. With sugar-derived glycals, 2-deoxy-2-halo-pyranosyl acetates or azides are generated in excellent yield. Free hydroxy groups are tolerated. Even, fully unprotected glucal 23 can be employed for the short synthesis of 2-deoxy-2-iodo glycosyl acetates 24a,b.
UR - http://www.scopus.com/inward/record.url?scp=0033579602&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(99)01925-5
DO - 10.1016/S0040-4039(99)01925-5
M3 - Article
AN - SCOPUS:0033579602
VL - 40
SP - 8999
EP - 9002
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 51
ER -