Abstract
The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 367-375 |
| Number of pages | 9 |
| Journal | Carbohydrate Research |
| Volume | 339 |
| Issue number | 2 |
| DOIs | |
| State | Published - Jan 22 2004 |
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ASJC Scopus subject areas
- Biochemistry
- Molecular Biology
- Organic Chemistry
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Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids. / Ying, Laiqiang; Gervay-Hague, Jacquelyn.
In: Carbohydrate Research, Vol. 339, No. 2, 22.01.2004, p. 367-375.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids
AU - Ying, Laiqiang
AU - Gervay-Hague, Jacquelyn
PY - 2004/1/22
Y1 - 2004/1/22
N2 - The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.
AB - The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.
UR - http://www.scopus.com/inward/record.url?scp=0346154803&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0346154803&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2003.10.018
DO - 10.1016/j.carres.2003.10.018
M3 - Article
C2 - 14698895
AN - SCOPUS:0346154803
VL - 339
SP - 367
EP - 375
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 2
ER -