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Glycan Syntheses |
JCGG ID |
JCGG-RAC0002383 | ||||
Submitter |
The Noguchi Institute | ||||
Reaction ID |
R-0000-002383
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Regist Date |
2012/06/21 19:08:11 | ||||
| REACTANT | |||||
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Reactant Type |
mannopyranoside | ||||
Mol |
7.56 mmol | ||||
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Reactant Type |
Me2SnCl2 | ||||
Mol |
0.37 mmol | ||||
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Reactant Type |
DIPEA | ||||
Mol |
15.13 mmol | ||||
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Reactant Type |
BzCl | ||||
Mol |
8.32 mmol | ||||
| PRODUCT | |||||
MOLECULE ID |
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Yield |
92% | ||||
| REACTION DETAIL | |||||
Reaction Time |
2.5 hours | ||||
Reaction Temp |
room temp | ||||
Solvent |
THF/H2O = 19/1 | ||||
Comment |
Me2SnCl2, DIPEA, and mannopyranoside were mixed and stirred for 5 minutes before the reaction. | ||||
| COMMENT | |||||
| Keywords: mannose, glucosamine, galactosamine, thioglycosides, 3-O-acylation, 4,6-O-benzylidenation, azide displacement, Lattrell-Dax inversion | |||||
| 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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