JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002524
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002524
Regist Date
 2012/06/21 19:23:47
REACTANT
MOLECULE ID
 JCGG-COM0000303 (Reaction Tree)
Reactant Type
 donor
Mol
 1 equiv.
MOLECULE ID
 JCGG-COM0001778
Reactant Type
 acceptor
Mol
 2 equiv.
MOLECULE ID
 JCGG-COM0003299
Reactant Type
 triphenylphosphine oxide
Mol
 3.3 equiv.
MOLECULE ID
 JCGG-COM0000761
Reactant Type
 Tf2O
Mol
 1.1 equiv.
PRODUCT
MOLECULE ID
 JCGG-COM0003304 (Reaction Tree)
Skeleton
JCGG-STR032526
Product Type
 alpha
Yield
 44%(alpha/beta=63/37)
MOLECULE ID
 JCGG-COM0003305 (Reaction Tree)
Skeleton
JCGG-STR031555
Product Type
 beta
Yield
 44%(alpha/beta=63/37)
MOLECULE ID
 JCGG-COM0003306 (Reaction Tree)
Product Type
 delta3,5-cholestadiene
Yield
 NOT specified
MOLECULE ID
 JCGG-COM0003307 (Reaction Tree)
Product Type
 cholesteryl ether
Yield
 NOT specified
REACTION DETAIL
Reaction Time
 NOT specified
Reaction Temp
 0 degree C
Solvent
 CH2Cl2
Comment
 Very few were described regarding this reaction.
COMMENT
Keywords: the Hendrickson reagent, dehydrative glycosylation, 1-hydroxyglycosyl donors, anomeric oxophosphonium intermediate
The details regarding this reaction are described in another paper in References.
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)