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Glycan Syntheses |
JCGG ID |
JCGG-RAC0002532 | ||||
Submitter |
The Noguchi Institute | ||||
Reaction ID |
R-0000-002532
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Regist Date |
2012/06/21 19:25:04 | ||||
| REACTANT | |||||
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Reactant Type |
Donor | ||||
Mol |
2 equiv. | ||||
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Reactant Type |
Acceptor | ||||
Mol |
1 equiv. | ||||
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Reactant Type |
triphenylphosphine oxide | ||||
Mol |
6.75 equiv. | ||||
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Reactant Type |
Tf2O | ||||
Mol |
3 equiv. | ||||
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Reactant Type |
DIEA | ||||
Mol |
3.3 + 3.3 equiv. | ||||
| PRODUCT | |||||
MOLECULE ID |
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Product Type |
alpha | ||||
Yield |
72% | ||||
| REACTION DETAIL | |||||
Reaction Time |
30 minutes, 30 minutes, up to 15 minutes | ||||
Reaction Temp |
0 degree C, -20 degree C, -20 degree C | ||||
Solvent |
dry CH2Cl2, dry CH2Cl2, dry CH2Cl2 | ||||
Comment |
1) triphenylphosphine oxide+Tf2O, 2) +Donor, DIEA, 3) +Acceptor, DIEA | ||||
| DIEA was added twice. (second phase, third phase) | |||||
| COMMENT | |||||
| Keywords: the Hendrickson reagent, dehydrative glycosylation, 1-hydroxyglycosyl donors, anomeric oxophosphonium intermediate | |||||
| There are multiple phases in this reaction. | |||||
| REFERENCE | |||||
Reference Id |
REF-0000-000351 | ||||
Issn |
Electronic | ||||
Doi |
10.1021/jo2015856 | ||||
PubMed ID |
21970416 | ||||
Journal Name |
The Journal of organic chemistry. (2011) 76 (21): 9122-6. | ||||
Article Title |
Dehydrative glycosylation with the Hendrickson reagent. | ||||
Author |
Matteo, Mossotti; Luigi, Panza | ||||
Affiliation |
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Via Bovio 6, 28100 Novara, Italy. | ||||
Reference Id |
REF-0000-000352 | ||||
Source |
J. Org. Chem. 2011, 76, 9122-9126 | ||||
Doi |
10.1021/jo2015856 | ||||
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)
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