JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002262
Submitter
The Noguchi Institute
Reaction ID
R-0000-002262
Regist Date
2012/06/21 18:55:05
REACTANT
MOLECULE ID
JCGG-COM0002908 (Reaction Tree)
Reactant Type
donor
Mol
1.2 equiv.
MOLECULE ID
JCGG-COM0001800 (Reaction Tree)
Skeleton
JCGG-STR032525
Reactant Type
acceptor
Mol
1.0 equiv.
MOLECULE ID
JCGG-COM0000009
Reactant Type
TMSOTf
Mol
0.15 equiv.
PRODUCT
MOLECULE ID
JCGG-COM0002933 (Reaction Tree)
Product Type
alpha
Yield
66%(alpha/beta=6/1)
MOLECULE ID
JCGG-COM0002934 (Reaction Tree)
Product Type
beta
Yield
66%(alpha/beta=6/1)
REACTION DETAIL
Reaction Time
NOT specified
Reaction Temp
room temp
Solvent
anhydrous CH2Cl2
Comment
Activated molecular sieves (50 mg/mL solvent) were included in the solvent.
The donor, the acceptor, and activated molecular sieves were mixed and stirred for 0.5 hour at room temperature before the reaction.
COMMENT
Keywords: stereoselectivity, 2-azido-2-deoxygalactosyl donors, acetyl groups, temperature, computational methods
REFERENCE
Reference Id
REF-0000-000327
Issn
Electronic
Doi
10.1021/jo1025157
PubMed ID
21574599
Journal Name
The Journal of organic chemistry. (2011) 76 (13): 5207-18.
Article Title
Study of the stereoselectivity of 2-azido-2-deoxygalactosyl donors: remote protecting group effects and temperature dependency.
Author
Jane, Kalikanda; Zhitao, Li
Affiliation
Department of Chemistry, Binghamton University, Binghamton, New York 13902, United States.
Reference Id
REF-0000-000328
Source
J. Org. Chem. 2011, 76, 5207-5218
Doi
10.1021/jo1025157

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