JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002423
Submitter
The Noguchi Institute
Reaction ID
R-0000-002423
Regist Date
2012/06/21 19:13:03
REACTANT
MOLECULE ID
JCGG-COM0003150 (Reaction Tree)
Reactant Type
sugar
Mol
0.1 mmol
MOLECULE ID
JCGG-COM0000491
Reactant Type
AcOH (solvent)
Volume
10 mL
MOLECULE ID
JCGG-COM0000086
Reactant Type
Ac2O
Mol
0.4 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003151 (Reaction Tree)
Yield
85%
REACTION DETAIL
Reaction Time
3 hours, 2 hours
Reaction Temp
65 degree C, 0 degree C
Solvent
glacial AcOH, pyridine
Comment
1) sugar+AcOH, 2) +Ac2O
COMMENT
Keywords: xylomannan, antifreeze, Alaskan beetle, Upis ceramboides
There are multiple phases in this reaction.
ATTENTION: Although NOT mentioned in the written method, Ac2O seems to be the correct compound to be used instead of BzCl.
REFERENCE
Reference Id
REF-0000-000339
Issn
Electronic
Doi
10.1021/jo201780e
PubMed ID
21955117
Journal Name
The Journal of organic chemistry. (2011) 76 (21): 8611-20.
Article Title
Synthesis and structural verification of the xylomannan antifreeze substance from the freeze-tolerant Alaskan beetle Upis ceramboides.
Author
David, Crich; Md Yeajur, Rahaman
Affiliation
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States. dcrich@chem.wayne.edu
Reference Id
REF-0000-000340
Source
J. Org. Chem. 2011, 76, 8611-8620
Doi
10.1021/jo201780e

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