JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002169
Submitter
The Noguchi Institute
Reaction ID
R-0000-002169
Regist Date
2012/06/21 18:44:27
REACTANT
MOLECULE ID
JCGG-COM0002814 (Reaction Tree)
Mol
0.28 mmol
MOLECULE ID
JCGG-COM0002816 (Reaction Tree)
Reactant Type
trichloroacetimidate
Mol
0.28 mmol
MOLECULE ID
JCGG-COM0000009
Reactant Type
TMSOTf
Volume
10 micro L
PRODUCT
MOLECULE ID
JCGG-COM0002817 (Reaction Tree)
Yield
91%
REACTION DETAIL
Reaction Time
1 hour
Reaction Temp
room temp
Solvent
dry CH2Cl2
Comment
MS 4A was included in the solvent.
The donor, the acceptor, and MS 4A were mixed and stirred for 30 minutes before the reaction.
COMMENT
Keywords: N,O-dimethyloxyamine-N-glycosides, protecting group manipulations, N-chlorosuccinimide, NCS, thioglycoside, trichloroacetimidate, complex oligosaccharide synthesis
REFERENCE
Reference Id
REF-0000-000323
Issn
Electronic
Doi
10.1021/jo102372m
PubMed ID
21332162
Journal Name
The Journal of organic chemistry. (2011) 76 (6): 1918-21.
Article Title
Use of N,O-dimethylhydroxylamine as an anomeric protecting group in carbohydrate synthesis.
Author
Somnath, Dasgupta; Mark, Nitz
Affiliation
Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, Canada M5S 3H6.
Reference Id
REF-0000-000324
Source
J. Org. Chem. 2011, 76, 1918-1921
Doi
10.1021/jo102372m

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