JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001573
Submitter
The Noguchi Institute
Reaction ID
R-0000-001573
Regist Date
2012/06/21 17:22:28
REACTANT
MOLECULE ID
JCGG-COM0001719 (Reaction Tree)
Reactant Type
glucopyranoside
Mol
3.75 mmol
MOLECULE ID
JCGG-COM0001650
Reactant Type
Br2 (in CH2Cl2, 1/165 in volume)
Volume
36 mL
MOLECULE ID
JCGG-COM0002012 (Reaction Tree)
Reactant Type
KSBiz
Mol
9.36 mmol
MOLECULE ID
JCGG-COM0000764
Reactant Type
18-crown-6
Mol
0.75 mmol
PRODUCT
MOLECULE ID
JCGG-COM0002007 (Reaction Tree)
Yield
73%
REACTION DETAIL
Reaction Time
5 minutes, 16 hours
Reaction Temp
room temp, room temp
Solvent
CH2Cl2, MeCN
Comment
1) glucopyranoside+Br2, MS 3A, 2) +all the rest
The glucopyranoside and MS 3A were mixed and stirred for 1 hour at room temperature before the reaction.
COMMENT
Keywords: carbohydrates, glycosides, glycosylation, oligosaccharides, synthetic methods
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000187
Issn
Electronic
Doi
10.1002/anie.201007212
PubMed ID
21433229
Journal Name
Angewandte Chemie (International ed. in English). (2011) 50 (18): 4197-201.
Article Title
S-Benzimidazolyl glycosides as a platform for oligosaccharide synthesis by an active-latent strategy.
Author
Scott J, Hasty; Matthew A, Kleine; Alexei V, Demchenko
Affiliation
Department of Chemistry and Biochemistry, University of Missouri-St.?Louis, One University Boulevard, St.?Louis, MO 63121, USA.
Reference Id
REF-0000-000188
Source
Angew. Chem. Int. Ed. 2011, 50, 4197-4201
Doi
10.1002/anie.201007212

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