JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002258
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002258
Regist Date
 2012/06/21 18:54:48
REACTANT
MOLECULE ID
 JCGG-COM0002886 (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-COM0002887 (Reaction Tree)
Product Type
 alpha
Yield
 75%(alpha/beta=11/1)
MOLECULE ID
 JCGG-COM0002888 (Reaction Tree)
Product Type
 beta
Yield
 75%(alpha/beta=11/1)
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)