JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002530
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002530
Regist Date
 2012/06/21 19:24:43
REACTANT
MOLECULE ID
 JCGG-COM0000046 (Reaction Tree)
Reactant Type
 Donor
Mol
 2 equiv.
MOLECULE ID
 JCGG-COM0003314 (Reaction Tree)
Skeleton
JCGG-STR031569
Reactant Type
 Acceptor
Mol
 1 equiv.
MOLECULE ID
 JCGG-COM0003299
Reactant Type
 triphenylphosphine oxide
Mol
 6.75 equiv.
MOLECULE ID
 JCGG-COM0000761
Reactant Type
 Tf2O
Mol
 3 equiv.
MOLECULE ID
 JCGG-COM0000426
Reactant Type
 DIEA
Mol
 3.3 + 3.3 equiv.
PRODUCT
MOLECULE ID
 JCGG-COM0003317 (Reaction Tree)
Skeleton
JCGG-STR030596
Product Type
 alpha
Yield
 96%(alpha/beta=37/63)
MOLECULE ID
 JCGG-COM0003318 (Reaction Tree)
Skeleton
JCGG-STR018184
Product Type
 beta
Yield
 96%(alpha/beta=37/63)
REACTION DETAIL
Reaction Time
 30 minutes, 30 minutes, up to 15 minutes
Reaction Temp
 0 degree C, -20 degree C, -20 degree C
Solvent
 dry CH2Cl2, dry CH2Cl2, dry CH2Cl2
Comment
 1) triphenylphosphine oxide+Tf2O, 2) +Donor, DIEA, 3) +Acceptor, DIEA
DIEA was added twice. (second phase, third phase)
COMMENT
Keywords: the Hendrickson reagent, dehydrative glycosylation, 1-hydroxyglycosyl donors, anomeric oxophosphonium intermediate
There are multiple phases in this reaction.
REFERENCE
Reference Id
 REF-0000-000351
Issn
 Electronic
Doi
 10.1021/jo2015856
PubMed ID
 21970416
Journal Name
 The Journal of organic chemistry. (2011) 76 (21): 9122-6.
Article Title
 Dehydrative glycosylation with the Hendrickson reagent.
Author
 Matteo, Mossotti; Luigi, Panza
Affiliation
 Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Via Bovio 6, 28100 Novara, Italy.
Reference Id
 REF-0000-000352
Source
 J. Org. Chem. 2011, 76, 9122-9126
Doi
 10.1021/jo2015856
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)