JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002660
Submitter
The Noguchi Institute
Reaction ID
R-0000-002660
Regist Date
2012/06/21 19:35:53
REACTANT
MOLECULE ID
JCGG-COM0003464 (Reaction Tree)
Mol
28.8 mmol
MOLECULE ID
JCGG-COM0001169
Reactant Type
TBDMSOTf
Mol
144.7 mmol
MOLECULE ID
JCGG-COM0001344
Reactant Type
2,6-lutidine
Volume
50 mL
MOLECULE ID
JCGG-COM0000057
Reactant Type
MeOH
Volume
100 mL
PRODUCT
MOLECULE ID
JCGG-COM0003465 (Reaction Tree)
Yield
82%
REACTION DETAIL
Reaction Time
30 minutes, 20 hours, 10 minutes
Reaction Temp
0 degree C, 25 degree C, 25 degree C
Solvent
CH2Cl2 (400mL), CH2Cl2 (400mL), CH2Cl2 (400mL)
Comment
1) 18+TBDMSOTf, 2,6-lutidine, 2) temperature change, 3) +MeOH
COMMENT
Keywords: building block, ceramides, glycolipids, galactosyl-phytosphingosine, KRN7000
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000361
Issn
Electronic
Doi
10.1021/jo102064p
PubMed ID
21155575
Journal Name
The Journal of organic chemistry. (2011) 76 (1): 320-3.
Article Title
Synthesis of a versatile building block for the preparation of 6-N-derivatized α-galactosyl ceramides: rapid access to biologically active glycolipids.
Author
Peter J, Jervis; Liam R, Cox; Gurdyal S, Besra
Affiliation
School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, United Kingdom.
Reference Id
REF-0000-000362
Source
J. Org. Chem. 2011, 76, 320-323
Doi
10.1021/jo102064p

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