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Glycan Syntheses |
JCGG ID |
JCGG-RAC0002321 | ||||
Submitter |
The Noguchi Institute | ||||
Reaction ID |
R-0000-002321
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Regist Date |
2012/06/21 19:02:20 | ||||
| REACTANT | |||||
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Mol |
0.20 mmol | ||||
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Reactant Type |
TEMPO (in CH2Cl2) | ||||
Mol |
0.0025 mmol | ||||
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Reactant Type |
KBr (in the solution of saturated NaHCO3 in H2O) | ||||
Mol |
0.018 mmol | ||||
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Reactant Type |
TBAB (in the solution of saturated NaHCO3 in H2O) | ||||
Mol |
0.001 mmol | ||||
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Reactant Type |
NaHCO3 (saturated in H2O) | ||||
Volume |
0.4 mL | ||||
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Reactant Type |
NaOCl (12.5% w/v in the solution of saturated NaHCO3 in H2O) | ||||
Volume |
0.5 + 0.5 mL | ||||
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Reactant Type |
NaCl (saturated in H2O) | ||||
Volume |
0.4 mL | ||||
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Reactant Type |
CH(OMe)3 | ||||
Mol |
0.39 mmol | ||||
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Reactant Type |
SOCl2 | ||||
Mol |
0.20 mmol | ||||
| PRODUCT | |||||
MOLECULE ID |
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Yield |
76% | ||||
| REACTION DETAIL | |||||
Reaction Time |
10 + 30 + 15 minutes, 30 minutes | ||||
Reaction Temp |
0 degree C, room temp | ||||
Solvent |
CH2Cl2/H2O, anhydrous MeOH | ||||
Comment |
1) +all except CH(OMe)3 and SOCl2, 2) +CH(OMe)3, SOCl2 | ||||
| KBr and TBAB were mixed independently, and then poured into the reaction mixture. | |||||
| Both NaOCl and NaCl were added dropwise over 10 minutes. | |||||
| NaOCl was added twice. (first phase; 0 minutes, 40 minutes) | |||||
| The addition of CH(OMe)3 was performed before the addition of SOCl2. (second phase) | |||||
| COMMENT | |||||
| Keywords: 2-acylamino uronic acid, glycosyl phosphonates, oxidation, uronate 2-nitro-glycal, thermodynamic 1,2-trans-di-equatorial phosphonylation | |||||
| There are multiple phases in this reaction. | |||||
| REFERENCE | |||||
Reference Id |
REF-0000-000331 | ||||
Issn |
Electronic | ||||
Doi |
10.1021/jo2002193 | ||||
PubMed ID |
21495699 | ||||
Journal Name |
The Journal of organic chemistry. (2011) 76 (10): 4099-104. | ||||
Article Title |
Accessing C-1 phosphonylated 2-acylamino uronic acids via 2-nitro-glycals. | ||||
Author |
Beenu, Bhatt; Robin J, Thomson; Mark, von Itzstein | ||||
Affiliation |
Institute for Glycomics, Griffith University, Gold Coast Campus, Queensland 4222, Australia. | ||||
Reference Id |
REF-0000-000332 | ||||
Source |
J. Org. Chem. 2011, 76, 4099-4104 | ||||
Doi |
10.1021/jo2002193 | ||||
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)
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