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Glycan Syntheses |
JCGG ID |
JCGG-RAC0002474 | ||||
Submitter |
The Noguchi Institute | ||||
Reaction ID |
R-0000-002474
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Regist Date |
2012/06/21 19:17:41 | ||||
| REACTANT | |||||
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Mol |
0.087 mmol | ||||
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Reactant Type |
propargyl alcohol | ||||
Mol |
17.8 mmol | ||||
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Reactant Type |
Cl3CCN | ||||
Mol |
19.6 mmol | ||||
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Reactant Type |
Na | ||||
Mol |
catalytic amount | ||||
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Reactant Type |
TfOH | ||||
Mol |
catalytic amount | ||||
| PRODUCT | |||||
MOLECULE ID |
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Yield |
49% | ||||
| REACTION DETAIL | |||||
Reaction Time |
3 hours, overnight | ||||
Reaction Temp |
room temp, room temp | ||||
Solvent |
none, CH2Cl2 (5mL) | ||||
Comment |
1) propargyl alcohol+Cl3CCN, Na, 2) +2a, TfOH, molecular sieves powder | ||||
| The reactants were mixed at 0 degree in Celsius before stirred at room temperature. (first phase) | |||||
| Molecular sieves powder was included in the solvent. (second phase) | |||||
| COMMENT | |||||
| Keywords: triazole, heparosan, chondroitin, copper catalyzed azide-alkyne cycloaddition, CuAAC, azido-glucuronic acid, glucosamine, galactosamine | |||||
| There are multiple phases in this reaction. | |||||
| REFERENCE | |||||
Reference Id |
REF-0000-000343 | ||||
Issn |
Electronic | ||||
Doi |
10.1021/jo200076z | ||||
PubMed ID |
21438620 | ||||
Journal Name |
The Journal of organic chemistry. (2011) 76 (9): 3181-93. | ||||
Article Title |
Design and synthesis of unnatural heparosan and chondroitin building blocks. | ||||
Author |
Smritilekha, Bera; Robert J, Linhardt | ||||
Affiliation |
Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New York 12180, USA. | ||||
Reference Id |
REF-0000-000344 | ||||
Source |
J. Org. Chem. 2011, 76, 3181-3193 | ||||
Doi |
10.1021/jo200076z | ||||
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)
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