JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001233
Submitter
The Noguchi Institute
Reaction ID
R-0000-001239
Regist Date
2012/06/21 16:46:36
REACTANT
MOLECULE ID
JCGG-COM0001389 (Reaction Tree)
Reactant Type
(in 15 mL of THF)
Mol
2.2 mmol
MOLECULE ID
JCGG-COM0001022
Reactant Type
TBAF (1 M in THF)
Volume
4.7 mL
MOLECULE ID
JCGG-COM0000160
Reactant Type
NaH
Mol
6.6 mmol
MOLECULE ID
JCGG-COM0000161
Reactant Type
BnBr
Mol
6.6 mmol
PRODUCT
MOLECULE ID
JCGG-COM0001392 (Reaction Tree)
Yield
61%
REACTION DETAIL
Reaction Time
30 minutes, 18 hours
Reaction Temp
room temp, room temp
Solvent
THF, THF
Comment
1) 16a+TBAF, 2) +all the rest
NaH and BnBr were added dropwise.
COMMENT
Keywords: galactal derivatives, 6-O-TIPS protection, trichloroacetimidates, Michael-type addition, 2-nitroglycals
There are two 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)