|
Glycan Syntheses |
JCGG ID |
JCGG-RAC0002229 | ||||
Submitter |
The Noguchi Institute | ||||
Reaction ID |
R-0000-002229
|
||||
Regist Date |
2012/06/21 18:52:26 | ||||
| REACTANT | |||||
|
|
|
||||
Reactant Type |
triol | ||||
Mol |
6.8 mmol | ||||
|
|
|
||||
Reactant Type |
NaH (60% in mineral oil) | ||||
Mol |
15.05 mmol | ||||
|
|
|
||||
Reactant Type |
BnBr | ||||
Mol |
15.05 mmol | ||||
| PRODUCT | |||||
MOLECULE ID |
|
|
|||
Product Type |
4,6-di-O-benzyl-D-galactal | ||||
Yield |
26% | ||||
| REACTION DETAIL | |||||
Reaction Time |
2 hours, 3 hours | ||||
Reaction Temp |
0 degree C, 0 degree C | ||||
Solvent |
anhydrous DMF, anhydrous DMF | ||||
Comment |
1) +all except BnBr, 2) +BnBr | ||||
| BnBr was added dropwise and rapidly. | |||||
| The mixture was allowed to stand for the entire period. (second phase) | |||||
| COMMENT | |||||
| Keywords: stereoselectivity, 2-azido-2-deoxygalactosyl donors, acetyl groups, temperature, computational methods | |||||
| There are multiple phases in this reaction. | |||||
| 15% of another dibenzylated product and 30% of starting material were also obtained. | |||||
| REFERENCE | |||||
Reference Id |
REF-0000-000327 | ||||
Issn |
Electronic | ||||
Doi |
10.1021/jo1025157 | ||||
PubMed ID |
21574599 | ||||
Journal Name |
The Journal of organic chemistry. (2011) 76 (13): 5207-18. | ||||
Article Title |
Study of the stereoselectivity of 2-azido-2-deoxygalactosyl donors: remote protecting group effects and temperature dependency. | ||||
Author |
Jane, Kalikanda; Zhitao, Li | ||||
Affiliation |
Department of Chemistry, Binghamton University, Binghamton, New York 13902, United States. | ||||
Reference Id |
REF-0000-000328 | ||||
Source |
J. Org. Chem. 2011, 76, 5207-5218 | ||||
Doi |
10.1021/jo1025157 | ||||
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)
|