JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001298
Submitter
The Noguchi Institute
Reaction ID
R-0000-001298
Regist Date
2012/06/21 16:49:32
REACTANT
MOLECULE ID
JCGG-COM0001453 (Reaction Tree)
Reactant Type
donor
Mol
1.4 equiv.
MOLECULE ID
JCGG-COM0001460 (Reaction Tree)
Skeleton
JCGG-STR032525
Reactant Type
acceptor
Mol
1 equiv.
MOLECULE ID
JCGG-COM0000743
Reactant Type
DDQ
Mol
1.4 equiv.
MOLECULE ID
JCGG-COM0001346
Reactant Type
DTBMP
Mol
4 equiv.
MOLECULE ID
JCGG-COM0000741
Reactant Type
MeOTf
Mol
3.5 equiv.
PRODUCT
MOLECULE ID
JCGG-COM0001461 (Reaction Tree)
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)