Abstract
Construction of aryl and heteroaryl N-glycoside structures by way of the palladium-catalyzed Buchwald-Hartwig N-arylation of pyranosylamines with aryl and heteroaryl halide derivatives is described. This methodology was successfully applied to the total synthesis of nucleoside antibiotics, spicamycin and dapiramicin B, possessing novel heteroaryl N-glycosides. Kinetic and thermodynamic analyses of heteroaryl N-glycosides are also reported.
| Original language | English |
|---|---|
| Pages (from-to) | 1105-1115 |
| Number of pages | 11 |
| Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
| Volume | 66 |
| Issue number | 11 |
| Publication status | Published - 2008 Nov |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Total synthesis of nucleoside antibiotics possessing novel N-glycoside structures. / Chida, Noritaka.
In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 66, No. 11, 11.2008, p. 1105-1115.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Total synthesis of nucleoside antibiotics possessing novel N-glycoside structures
AU - Chida, Noritaka
PY - 2008/11
Y1 - 2008/11
N2 - Construction of aryl and heteroaryl N-glycoside structures by way of the palladium-catalyzed Buchwald-Hartwig N-arylation of pyranosylamines with aryl and heteroaryl halide derivatives is described. This methodology was successfully applied to the total synthesis of nucleoside antibiotics, spicamycin and dapiramicin B, possessing novel heteroaryl N-glycosides. Kinetic and thermodynamic analyses of heteroaryl N-glycosides are also reported.
AB - Construction of aryl and heteroaryl N-glycoside structures by way of the palladium-catalyzed Buchwald-Hartwig N-arylation of pyranosylamines with aryl and heteroaryl halide derivatives is described. This methodology was successfully applied to the total synthesis of nucleoside antibiotics, spicamycin and dapiramicin B, possessing novel heteroaryl N-glycosides. Kinetic and thermodynamic analyses of heteroaryl N-glycosides are also reported.
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M3 - Article
AN - SCOPUS:60249103759
VL - 66
SP - 1105
EP - 1115
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 11
ER -