JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002427
Submitter
The Noguchi Institute
Reaction ID
R-0000-002427
Regist Date
2012/06/21 19:13:25
REACTANT
MOLECULE ID
JCGG-COM0003155 (Reaction Tree)
Skeleton
JCGG-STR032527
Mol
1.0 equiv.
MOLECULE ID
JCGG-COM0001980
Reactant Type
benzyl 2,2,2-trichloroacetimidate
Mol
4.0 equiv.
MOLECULE ID
JCGG-COM0000111
Reactant Type
TfOH
Mol
0.05 equiv.
MOLECULE ID
JCGG-COM0000411
Reactant Type
KOH
Mol
NOT specified
PRODUCT
MOLECULE ID
JCGG-COM0003156 (Reaction Tree)
Skeleton
JCGG-STR032527
Yield
77%
REACTION DETAIL
Reaction Time
4 hours, 3 hours
Reaction Temp
room temp, reflux
Solvent
cyclohexane/CH2Cl2 = 4/1, MeOH
Comment
1) +all except KOH, 2) +KOH
COMMENT
Keywords: acylation, pivaloylation, pivaloyl chloride, esterifying, regioisomers
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000341
Issn
Electronic
PubMed ID
11672212
Journal Name
The Journal of organic chemistry. (1998) 63 (17): 6035-6038.
Article Title
Regioselective Acylation of Hexopyranosides with Pivaloyl Chloride.
Author
Lu, Jiang; Tak-Hang, Chan
Affiliation
Department of Chemistry, McGill University, Montréal, Québec H3A 2K6, Canada.
Reference Id
REF-0000-000342
Source
J. Org. Chem. 1998, 63, 6035-6038
Doi
10.1021/jo980294v

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