Details
| Original language | English |
|---|---|
| Pages (from-to) | 3623-3626 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 3 |
| Issue number | 23 |
| Publication status | Published - 13 Oct 2001 |
Abstract
Figure presented A glycosylation protocol for the synthesis of 2-deoxyglycosides has been developed which is based on the use of polymer-bound reagents. Glycals are transformed into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)iodate(I) complex (1). Activation of the anomeric center is achieved by employing polymer-bound silyl triflate (2). In the presence of different glycosyl acceptors, 2-deoxy-2-iodoglycosides are generated in very good yields. Furthermore, it is shown that this method can be embedded in multistep sequences toward glycosylated testosterone and rhodinosyl-olivosyl-olivoside.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic Letters, Vol. 3, No. 23, 13.10.2001, p. 3623-3626.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The first polymer-assisted solution-phase synthesis of deoxyglycosides
AU - Kirschning, Andreas
AU - Jesberger, Martin
AU - Schönberger, Andreas
PY - 2001/10/13
Y1 - 2001/10/13
N2 - Figure presented A glycosylation protocol for the synthesis of 2-deoxyglycosides has been developed which is based on the use of polymer-bound reagents. Glycals are transformed into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)iodate(I) complex (1). Activation of the anomeric center is achieved by employing polymer-bound silyl triflate (2). In the presence of different glycosyl acceptors, 2-deoxy-2-iodoglycosides are generated in very good yields. Furthermore, it is shown that this method can be embedded in multistep sequences toward glycosylated testosterone and rhodinosyl-olivosyl-olivoside.
AB - Figure presented A glycosylation protocol for the synthesis of 2-deoxyglycosides has been developed which is based on the use of polymer-bound reagents. Glycals are transformed into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)iodate(I) complex (1). Activation of the anomeric center is achieved by employing polymer-bound silyl triflate (2). In the presence of different glycosyl acceptors, 2-deoxy-2-iodoglycosides are generated in very good yields. Furthermore, it is shown that this method can be embedded in multistep sequences toward glycosylated testosterone and rhodinosyl-olivosyl-olivoside.
UR - http://www.scopus.com/inward/record.url?scp=0035891757&partnerID=8YFLogxK
U2 - 10.1021/ol016545v
DO - 10.1021/ol016545v
M3 - Article
C2 - 11700097
AN - SCOPUS:0035891757
VL - 3
SP - 3623
EP - 3626
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 23
ER -