JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001294
Submitter
The Noguchi Institute
Reaction ID
R-0000-001294
Regist Date
2012/06/21 16:49:18
REACTANT
MOLECULE ID
JCGG-COM0001454 (Reaction Tree)
Reactant Type
acetal
Mol
1 equiv.
MOLECULE ID
JCGG-COM0001346
Reactant Type
DTBMP
Mol
4 equiv.
MOLECULE ID
JCGG-COM0000741
Reactant Type
MeOTf
Mol
3.5 equiv.
MOLECULE ID
JCGG-COM0000110
Reactant Type
TFA
Volume
200 micro L
MOLECULE ID
JCGG-COM0000979
Reactant Type
pyridine
Volume
5.0 mL
MOLECULE ID
JCGG-COM0000086
Reactant Type
Ac2O
Volume
500 micro L
MOLECULE ID
JCGG-COM0000500
Reactant Type
DMAP
Mol
catalytic amount
PRODUCT
MOLECULE ID
JCGG-COM0001457 (Reaction Tree)
Product Type
beta
Yield
72%(beta only)
REACTION DETAIL
Reaction Time
NOT specified, 3 hours, 12 hours
Reaction Temp
50 degree C, 0 degree C, room temp
Solvent
(CH2Cl)2, CH2Cl2, CH2Cl2
Comment
1) acetal+DTBMP, MS 4A, MeOTf, 2) +TFA, 3) +all the rest
MS 4A was included in the solvent.
The reactants were mixed at room temperature before stirred at 50 degree in Celsius. (first phase)
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)