Journal ArticleDOI
Microwave-induced, Montmorillonite K10-catalyzed Ferrier rearrangement of tri-O-acetyl-d-galactal: mild, eco-friendly, rapid glycosidation with allylic rearrangement
Reads0
Chats0
TLDR
Montmorillonite K10 was found to catalyze, under microwave irradiation, rapid O-glycosidation of 3,4,6-tri-O-acetyl-d-galactal to afford exclusively the alkyl and aryl 2,3-dideoxy-dthreo-hex-2-enopyranosides with very high α-selectivity as mentioned in this paper.About:
This article is published in Tetrahedron Letters.The article was published on 2002-09-16. It has received 46 citations till now. The article focuses on the topics: Ferrier rearrangement & Ferrier carbocyclization.read more
Citations
More filters
Journal ArticleDOI
Recent Developments in the Ferrier Rearrangement
TL;DR: A review of recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals can be found in this paper.
Journal ArticleDOI
Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals.
TL;DR: Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good alpha selectivity.
Journal ArticleDOI
Chemical O-Glycosylations: An Overview
TL;DR: This Review will focus on the key developments towards chemical O‐glycosylations in the current century, including synthesis of novel glycosyl donors and acceptors and their unique activation for successful glycosidic bonds.
Journal ArticleDOI
Application of clay catalysts in organic synthesis. a review
Sujaya Dasgupta,Béla Török +1 more
TL;DR: In this article, the application of clay catalyssts in ORGANIC SYNTHESIS is discussed. And a review of the application can be found in the Appendix.
Journal ArticleDOI
Ferric sulfate hydrate-catalyzed O-glycosylation using glycals with or without microwave irradiation
TL;DR: In this paper, a novel glycal-based O-glycosylation reaction, in which the substrates are not only peracetyl glycals but also perbenzyl glucals to afford the corresponding 2,3-unsaturated-O-glucosides via Ferrier rearrangement, was developed.
References
More filters
Journal ArticleDOI
Sur l'isomérisation du 1,5-anhydro-3,4,6-tri-O-benzyl-1,2-didésoxy-d-arabino-hex-1-énitol on présence d'acides de Lewis
Journal ArticleDOI
Practical Glycosidation Method of Glycals Using Montmorillonite K-10 as an Environmentally Acceptable and Inexpensive Industrial Catalyst
Journal ArticleDOI
Lithium perchlorate-assisted substitution reactions of allylic acetates and allylic alcohols
TL;DR: Substitution reactions of allylic acetates and allylic alcohols by a variety of nucleophiles proceed smoothly in the presence of lithium perchlorate in ether, providing a convenient alternative to transition metal catalyzed methods as discussed by the authors.
Journal ArticleDOI
Microwave Induced Ferrier Rearrangement
S. Sowmya,K. K. Balasubramanian +1 more
TL;DR: In this paper, a short and facile entry to the 2, 3-unsaturated O-aryl glyco sides via microwave induced Ferrier rearrangement of acetylated glucal is reported.
Journal ArticleDOI
Reaction of 2,3-unsaturated aryl glycosides with lewis acids : a convenient entry to C-aryl glycosides
TL;DR: In this article, a facile synthesis of 2,3-unsaturated aryl glycosides by BF 3.Et 2 O mediated O to C transformation was reported.
Related Papers (5)
Indium trichloride catalyzed glycosidation. An expeditious synthesis of 2,3-unsaturated glycopyranosides†
Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals.
Stereoselective palladium-catalyzed O-glycosylation using glycals
Hahn Kim,Hongbin Men,Chulbom Lee +2 more