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Glycan Syntheses |
JCGG ID |
JCGG-RAC0002390 | ||||
Submitter |
The Noguchi Institute | ||||
Reaction ID |
R-0000-002390
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Regist Date |
2012/06/21 19:08:47 | ||||
| REACTANT | |||||
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Mol |
0.27 mmol | ||||
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Reactant Type |
Tf2O | ||||
Mol |
0.54 mmol | ||||
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Reactant Type |
pyridine | ||||
Mol |
0.54 mmol | ||||
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Reactant Type |
TBANO2 | ||||
Mol |
0.81 mmol | ||||
| PRODUCT | |||||
MOLECULE ID |
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Yield |
73% | ||||
| REACTION DETAIL | |||||
Reaction Time |
2 + 10 minutes, 1 hour | ||||
Reaction Temp |
0 degree C, room temp | ||||
Solvent |
CH2Cl2, MeCN | ||||
Comment |
1) +all except TBANO2, 2) +TBANO2 | ||||
| Tf2O was added dropwise. | |||||
| Pyridine was added 2 minutes after the initiation of the reaction. (first phase) | |||||
| COMMENT | |||||
| Keywords: mannose, glucosamine, galactosamine, thioglycosides, 3-O-acylation, 4,6-O-benzylidenation, azide displacement, Lattrell-Dax inversion | |||||
| There are multiple phases in this reaction. | |||||
| REFERENCE | |||||
Reference Id |
REF-0000-000337 | ||||
Issn |
Electronic | ||||
Doi |
10.1021/jo200342v | ||||
PubMed ID |
21510706 | ||||
Journal Name |
The Journal of organic chemistry. (2011) 76 (11): 4703-9. | ||||
Article Title |
Rapid transformation of D-mannose into orthogonally protected D-glucosamine and D-galactosamine thioglycosides. | ||||
Author |
Madhu, Emmadi; Suvarn S, Kulkarni | ||||
Affiliation |
Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, India. | ||||
Reference Id |
REF-0000-000338 | ||||
Source |
J. Org. Chem. 2011, 76, 4703-4709 | ||||
Doi |
10.1021/jo200342v | ||||
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)
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