JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0001300
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-001300
Regist Date
 2012/06/21 16:49:39
REACTANT
MOLECULE ID
 JCGG-COM0001453 (Reaction Tree)
Reactant Type
 donor
Mol
 1.4 equiv.
MOLECULE ID
 JCGG-COM0001464 (Reaction Tree)
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-COM0001465 (Reaction Tree)
Skeleton
JCGG-STR019779
Product Type
 beta
Yield
 71%(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)