JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001235
Submitter
The Noguchi Institute
Reaction ID
R-0000-001241
Regist Date
2012/06/21 16:46:41
REACTANT
MOLECULE ID
JCGG-COM0001392 (Reaction Tree)
Reactant Type
glycal (in 10 mL of Ac2O)
Mol
0.23 mmol
MOLECULE ID
JCGG-COM0001374
Reactant Type
HNO3 (in 50 mL of Ac2O)
Mol
3.82 equiv.
PRODUCT
MOLECULE ID
JCGG-COM0001394 (Reaction Tree)
Yield
63%
REACTION DETAIL
Reaction Time
10 to 15 minutes + 1 hour
Reaction Temp
-30 degree C
Solvent
Ac2O
Comment
Before the reaction, concentrated HNO3 was added dropwise to Ac2O at 10 degree in Celsius under constant stirring.
The glycal was added over a period of 10 to 15 minutes.
COMMENT
Keywords: galactal derivatives, 6-O-TIPS protection, trichloroacetimidates, Michael-type addition, 2-nitroglycals
REFERENCE
Reference Id
REF-0000-000063
Issn
Print
Doi
10.1021/jo061670b
PubMed ID
17503844
Journal Name
The Journal of organic chemistry. (2007) 72 (12): 4367-77.
Article Title
Glycal glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis.
Author
Jürgen, Geiger; B Gopal, Reddy; Gottfried A, Winterfeld; R, Weber; M, Przybylski; R R, Schmidt
Affiliation
Fachbereich Chemie, Universität Konstanz, Fach M 725, D - 78457 Konstanz, Germany.
Reference Id
REF-0000-000064
Source
J. Org. Chem. 2007, 72, 4367-4377
Doi
10.1021/jo061670b

©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)