|
Glycan Syntheses |
JCGG ID |
JCGG-RAC0002164 | ||||
Submitter |
The Noguchi Institute | ||||
Reaction ID |
R-0000-002164
|
||||
Regist Date |
2012/06/21 18:43:59 | ||||
| REACTANT | |||||
|
|
|
||||
Reactant Type |
N-acetyl-glucosamine | ||||
Mol |
4.52 mmol | ||||
|
|
|
||||
Reactant Type |
MeHNOMe*HCl | ||||
Mol |
4.97 mmol | ||||
|
|
|
||||
Reactant Type |
NaOAc | ||||
Mol |
4.97 mmol | ||||
|
|
|
||||
Reactant Type |
NaH | ||||
Mol |
18.08 mmol | ||||
|
|
|
||||
Reactant Type |
BnBr | ||||
Mol |
20.4 mmol | ||||
| PRODUCT | |||||
MOLECULE ID |
|
|
|||
Yield |
64% | ||||
| REACTION DETAIL | |||||
Reaction Time |
20 hours, 1 hour | ||||
Reaction Temp |
room temp, room temp | ||||
Solvent |
H2O, DMF | ||||
Comment |
1) +all except NaH and BnBr 2) +NaH, BnBr | ||||
| The reactants were mixed at 0 degree in Celsius before stirred at room temperature. (first phase) | |||||
| COMMENT | |||||
| Keywords: N,O-dimethyloxyamine-N-glycosides, protecting group manipulations, N-chlorosuccinimide, NCS, thioglycoside, trichloroacetimidate, complex oligosaccharide synthesis | |||||
| There are multiple phases in this reaction. | |||||
| REFERENCE | |||||
Reference Id |
REF-0000-000323 | ||||
Issn |
Electronic | ||||
Doi |
10.1021/jo102372m | ||||
PubMed ID |
21332162 | ||||
Journal Name |
The Journal of organic chemistry. (2011) 76 (6): 1918-21. | ||||
Article Title |
Use of N,O-dimethylhydroxylamine as an anomeric protecting group in carbohydrate synthesis. | ||||
Author |
Somnath, Dasgupta; Mark, Nitz | ||||
Affiliation |
Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, Canada M5S 3H6. | ||||
Reference Id |
REF-0000-000324 | ||||
Source |
J. Org. Chem. 2011, 76, 1918-1921 | ||||
Doi |
10.1021/jo102372m | ||||
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)
|