Details
| Original language | English |
|---|---|
| Pages (from-to) | 3435-3446 |
| Number of pages | 12 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 16 |
| Publication status | Published - 3 Aug 2004 |
Abstract
Polymer-bound diphenylphosphane hydrobromide 2 shows excellent properties in the activation of enol ethers and glycals, the introduction and cleavage of THP ethers being promoted with excellent yields with this functionalized polymer, Glycosidations of glycals work equally well, with suppression of the formation of undesired Ferrier rearranged products. The reagent is sufficiently mild to leave labile 2-deoxy glycosidic bonds and acid-labile protecting groups intact. It can be employed to transfer disaccharide glycosyl donors onto aglycons and is also selective for the promotion of two glycosidations in one pot, Highly hindered glycosyl donor groups such as the hydroxy group at C-13 of the baccatin III framework can be glycosylated with glycals in the presence of this polymer-bound reagent.
Keywords
- Baccatin III, Glycoconjugates, Glycosidation, Multistep synthesis, Polymer-bound reagents, Protecting group
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. 16, 03.08.2004, p. 3435-3446.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Polymer-bound diphenylphosphane hydrobromide, a mild acid for the activation of enol ethers
T2 - Applications in polymer-assisted glycosidations
AU - Jaunzems, Janis
AU - Kashin, Dmitri
AU - Schönberger, Andreas
AU - Kirschning, Andreas
PY - 2004/8/3
Y1 - 2004/8/3
N2 - Polymer-bound diphenylphosphane hydrobromide 2 shows excellent properties in the activation of enol ethers and glycals, the introduction and cleavage of THP ethers being promoted with excellent yields with this functionalized polymer, Glycosidations of glycals work equally well, with suppression of the formation of undesired Ferrier rearranged products. The reagent is sufficiently mild to leave labile 2-deoxy glycosidic bonds and acid-labile protecting groups intact. It can be employed to transfer disaccharide glycosyl donors onto aglycons and is also selective for the promotion of two glycosidations in one pot, Highly hindered glycosyl donor groups such as the hydroxy group at C-13 of the baccatin III framework can be glycosylated with glycals in the presence of this polymer-bound reagent.
AB - Polymer-bound diphenylphosphane hydrobromide 2 shows excellent properties in the activation of enol ethers and glycals, the introduction and cleavage of THP ethers being promoted with excellent yields with this functionalized polymer, Glycosidations of glycals work equally well, with suppression of the formation of undesired Ferrier rearranged products. The reagent is sufficiently mild to leave labile 2-deoxy glycosidic bonds and acid-labile protecting groups intact. It can be employed to transfer disaccharide glycosyl donors onto aglycons and is also selective for the promotion of two glycosidations in one pot, Highly hindered glycosyl donor groups such as the hydroxy group at C-13 of the baccatin III framework can be glycosylated with glycals in the presence of this polymer-bound reagent.
KW - Baccatin III
KW - Glycoconjugates
KW - Glycosidation
KW - Multistep synthesis
KW - Polymer-bound reagents
KW - Protecting group
UR - http://www.scopus.com/inward/record.url?scp=4544234925&partnerID=8YFLogxK
U2 - 10.1002/ejoc.200400069
DO - 10.1002/ejoc.200400069
M3 - Article
AN - SCOPUS:4544234925
SP - 3435
EP - 3446
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 16
ER -