JCGG ID |
JCGG-RAC0001298 | |||||||
Submitter |
The Noguchi Institute | |||||||
Reaction ID |
R-0000-001298 | |||||||
Regist Date |
2012/06/21 16:49:32 | |||||||
REACTANT | ||||||||
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Reactant Type |
donor | |||||||
Mol |
1.4 equiv. | |||||||
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|
|
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Reactant Type |
acceptor | |||||||
Mol |
1 equiv. | |||||||
|
|
|||||||
Reactant Type |
DDQ | |||||||
Mol |
1.4 equiv. | |||||||
|
|
|||||||
Reactant Type |
DTBMP | |||||||
Mol |
4 equiv. | |||||||
|
|
|||||||
Reactant Type |
MeOTf | |||||||
Mol |
3.5 equiv. | |||||||
PRODUCT | ||||||||
MOLECULE ID |
|
|
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Product Type |
beta | |||||||
Yield |
64%(beta only) | |||||||
REACTION DETAIL | ||||||||
Reaction Time |
4 hours, 48 hours | |||||||
Reaction Temp |
0 degree C, room temp | |||||||
Solvent |
CH2Cl2, (CH2Cl)2 | |||||||
Comment |
1) donor+acceptor, MS 4A, DDQ, 2) +DTBMP, MS 4A, MeOTf | |||||||
MS 4A was included in the solvent. (added twice) | ||||||||
COMMENT | ||||||||
Keywords: beta-L-rhamnopyranosides, stereoselective synthesis, beta-D-mannopyranosides, intramolecular aglycon delivery, IAD | ||||||||
There are multiple phases in this reaction. | ||||||||
The alpha/beta ratio was determined by 1H NMR after isolation. | ||||||||
REFERENCE | ||||||||
Reference Id |
REF-0000-000065 | |||||||
Issn |
Electronic | |||||||
Doi |
10.1021/ja801574q | |||||||
PubMed ID |
18433121 | |||||||
Journal Name |
Journal of the American Chemical Society. (2008) 130 (20): 6330-1. | |||||||
Article Title |
Stereoselective synthesis of beta-L-rhamnopyranosides. | |||||||
Author |
Yong Joo, Lee; Akihiro, Ishiwata; Yukishige, Ito | |||||||
Affiliation |
RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. | |||||||
Reference Id |
REF-0000-000066 | |||||||
Source |
J. AM. CHEM. SOC. 2008, 130, 6330-6331 | |||||||
Doi |
10.1021/ja801574q |
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST) |