|
Glycan Syntheses |
JCGG ID |
JCGG-RAC0001403 | ||||
Submitter |
The Noguchi Institute | ||||
Reaction ID |
R-0000-001403
|
||||
Regist Date |
2012/06/21 16:58:34 | ||||
| REACTANT | |||||
|
|
|
||||
Reactant Type |
NeuAc-Lac/LacNAc | ||||
Mol |
16.0 micro mol | ||||
|
|
|
||||
Mol |
3.01 equiv. | ||||
|
|
|
||||
Reactant Type |
1H-tetrazole | ||||
Mol |
4.57 equiv. | ||||
|
|
|
||||
Reactant Type |
Me2S | ||||
Mol |
100 equiv. | ||||
|
|
|
||||
Reactant Type |
t-BuOOH | ||||
Mol |
9.83 equiv. | ||||
|
|
|
||||
Reactant Type |
DBU | ||||
Mol |
3.01 equiv. | ||||
|
|
|
||||
Reactant Type |
MeOH | ||||
Volume |
1.6 mL | ||||
|
|
|
||||
Reactant Type |
28% methanolic NaOMe | ||||
Volume |
16 micro L | ||||
| PRODUCT | |||||
MOLECULE ID |
|
|
|||
Yield |
60% | ||||
| REACTION DETAIL | |||||
Reaction Time |
more than 30 minutes, 3 hours, 5 minutes, 19 hours | ||||
Reaction Temp |
room temp, room temp, 0 degree C, room temp | ||||
Solvent |
dry MeCN, MeCN, MeCN, MeCN/MeOH | ||||
Comment |
1) NeuAc-Lac/LacNAc+6, 1H-tetrazole, 2) +Me2S, t-BuOOH, 3) +DBU, 4) +all the rest | ||||
| Before the reaction, NeuAc-Lac/LacNAc and 6 were dried by coevaporation with dry EtOAc. (2 times) | |||||
| The reactants were mixed at -40 degree in Celsius, and allowed to warm slowly to room temperature. (first phase) | |||||
| The reactants were mixed at 0 degree in Celsius before stirred at room temperature. (second and fourth phases) | |||||
| COMMENT | |||||
| Keywords: Bisubstrate-type sialyltransferase inhibitors, CMP-NeuAc, N-acetyllactosamine, lactose, sialic acid, ST6N, ST3N | |||||
| There are multiple phases in this reaction. | |||||
| REFERENCE | |||||
Reference Id |
REF-0000-000071 | ||||
Issn |
|||||
Doi |
10.1021/jo030042g | ||||
PubMed ID |
12839452 | ||||
Journal Name |
The Journal of organic chemistry. (2003) 68 (14): 5602-13. | ||||
Article Title |
Systematic syntheses and inhibitory activities of bisubstrate-type inhibitors of sialyltransferases. | ||||
Author |
Hiroshi, Hinou; Xue-Long, Sun; Yukishige, Ito | ||||
Affiliation |
RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan. | ||||
Reference Id |
REF-0000-000072 | ||||
Source |
J. Org. Chem. 2003, 68, 5602-5613 | ||||
Doi |
10.1021/jo030042g | ||||
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)
|