JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001277
Submitter
The Noguchi Institute
Reaction ID
R-0000-001277
Regist Date
2012/06/21 16:48:30
REACTANT
MOLECULE ID
JCGG-COM0001433 (Reaction Tree)
Mol
0.117 mol
MOLECULE ID
JCGG-COM0001022
Reactant Type
TBAF (1 M in THF)
Volume
352 mL
MOLECULE ID
JCGG-COM0000160
Reactant Type
NaH
Mol
0.352 mol
MOLECULE ID
JCGG-COM0000161
Reactant Type
BnBr
Mol
0.352 mol
MOLECULE ID
JCGG-COM0000491
Reactant Type
AcOH
Volume
300 mL
MOLECULE ID
JCGG-COM0000531
Reactant Type
H2O
Volume
80 mL
PRODUCT
MOLECULE ID
JCGG-COM0001434 (Reaction Tree)
Yield
63%
REACTION DETAIL
Reaction Time
2 hours, 12 hours, 24 hours
Reaction Temp
room temp, ice-bath, room temp
Solvent
THF, DMF, THF
Comment
1) 48+TBAF, 2) +NaH, BnBr, 3) +all the rest
COMMENT
Keywords: galactal derivatives, 6-O-TIPS protection, trichloroacetimidates, Michael-type addition, 2-nitroglycals
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000063
Issn
Print
Doi
10.1021/jo061670b
PubMed ID
17503844
Journal Name
The Journal of organic chemistry. (2007) 72 (12): 4367-77.
Article Title
Glycal glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis.
Author
Jürgen, Geiger; B Gopal, Reddy; Gottfried A, Winterfeld; R, Weber; M, Przybylski; R R, Schmidt
Affiliation
Fachbereich Chemie, Universität Konstanz, Fach M 725, D - 78457 Konstanz, Germany.
Reference Id
REF-0000-000064
Source
J. Org. Chem. 2007, 72, 4367-4377
Doi
10.1021/jo061670b

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