JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0001271
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-001271
Regist Date
 2012/06/21 16:48:12
REACTANT
MOLECULE ID
 JCGG-COM0001425 (Reaction Tree)
Mol
 0.122 mmol
MOLECULE ID
 JCGG-COM0000414
Reactant Type
 H2 (gas, 75 psi and normal)
MOLECULE ID
 JCGG-COM0000979
Reactant Type
 pyridine (solvent)
Volume
 4 mL
MOLECULE ID
 JCGG-COM0000086
Reactant Type
 Ac2O (solvent)
Volume
 2 mL, 1.33 mL
MOLECULE ID
 JCGG-COM0001022
Reactant Type
 TBAF (1 M in THF)
Volume
 0.1 mL, 0.66 mL
MOLECULE ID
 JCGG-COM0001026
Reactant Type
 Pd/C (10% palladium)
Weight
 0.02g
MOLECULE ID
 JCGG-COM0000110
Reactant Type
 TFA (solvent)
Volume
 1 mL
MOLECULE ID
 JCGG-COM0001037
Reactant Type
 CH2Cl2 (solvent)
Volume
 1 mL
MOLECULE ID
 JCGG-COM0001426
Reactant Type
 FmocONSu
Mol
 0.0278 mmol
MOLECULE ID
 JCGG-COM0000549
Reactant Type
 NaHCO3
Mol
 0.2780 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0001427 (Reaction Tree)
Skeleton
JCGG-STR025815
Yield
 56%
REACTION DETAIL
Reaction Time
 12 hours, 12 hours, 4 hours, 14 hours, 12 hours, 12 hours, 12 hours
Reaction Temp
 NOT specified, NOT specified, room temp, NOT specified, NOT specified, room temp, NOT specified
Solvent
 EtOH, pyridine/Ac2O = 2/1, THF, MeOH/AcOH = 4/1, pyridine/Ac2O = 2/1, THF/CH2Cl2, MeCN/H2O = 1/1
Catalyst
 platinized Raney nickel T4 (first phase)
Comment
 1) 41a+H2, 2) solvent change, 3) +TBAF, 4) +Pd/C, H2, 5) solvent change, 6) solvent change, 7) +FmocONSu, NaHCO3
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)