Journal ArticleDOI
Microwave-induced, Montmorillonite K10-catalyzed Ferrier rearrangement of tri-O-acetyl-d-galactal: mild, eco-friendly, rapid glycosidation with allylic rearrangement
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
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Journal ArticleDOI
Montmorillonite K-10 clay-catalyzed Ferrier rearrangement of 2-C-hydroxymethyl-d-glycals, 3,4,6-tri-O-alkyl-d-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol: a few unexpected domino transformations.
Elumalai Kumaran,Meenakshisundaram Santhi,Kalpattu K. Balasubramanian,Shanmugasundaram Bhagavathy +3 more
TL;DR: Reaction of 2-C-hydroxymethyl-d-galactal with 2,6-dimethylphenol in the presence of montmorillonite K-10 led to a novel domino transformation affording 4-(5',6'-dihydro-4H-pyran-3'-ylmethyl)-2, 6-dimmethylphenol, which led to totally unexpected transformations.
Journal ArticleDOI
Amberlyst 15–Catalyzed Efficient Synthesis of 2,3‐Unsaturated Glycosides via Ferrier Rearrangement for Glycal
TL;DR: Amberlyst 15 serves as an inexpensive, effective, and environmentally friendly catalyst in converting 3,4,6,tri-O-acetyl-D-glucal into 2,3,unsaturated O and S-glycosides via Ferrier rearrangement in moderate to excellent yields with high α selectivity as discussed by the authors.
Journal ArticleDOI
2,3-Unsaturated allyl glycosides as glycosyl donors for selective α-glycosylation.
TL;DR: In the presence of NBS and a catalytic amount of a Lewis acid, 2,3-unsaturated allyl glycosides have been successfully used as versatile glycosyl donors for the stereoselective α-glycosylation of a variety of alcohols comprising sensitive functions such as acetonide, keto, nitro, and ester in 50-90% yields.
Journal ArticleDOI
Methyl 1,2‐Orthoesters in Acid‐Washed Molecular Sieves Mediated Glycosylations
Clara Uriel,Patrícia Rijo,Patrícia Rijo,Ana Sofia Fernandes,Ana Sofia Fernandes,Ana M. Gómez,Bert Fraser-Reid,J. Cristobal Lopez +7 more
TL;DR: In this paper, the authors thank the Ministerio de Economia y Competitividad (MINECO, Spain), grant CTQ2015-66702-R for financial support
Book ChapterDOI
C=C Bond Formation
TL;DR: Stavudine has been recently approved as the fourth anti-HIV drug, which exhibits an effect comparable to that of AZT in HIV-infected CEM cells (in vivo), is less toxic than AZT, and was found to be less inhibitory to mitochondrial DNA replication.
References
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Journal ArticleDOI
Recent progress in O-glycosylation methods and its application to natural products synthesis
Kazunobu Toshima,Kuniaki Tatsuta +1 more
Book
The anomeric effect
Eusebio Juaristi,Gabriel Cuevas +1 more
TL;DR: This chapter discusses the history and applications of the Anomeric Effect in Organic Synthesis, and some of the applications can be found in the literature on endoelectronic effects of the anomeric effect.
Journal ArticleDOI
Unsaturated carbohydrates. Part IX. Synthesis of 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides from tri-O-acetyl-D-glucal
R. J. Ferrier,N. Prasad +1 more
TL;DR: Tri-O-acetyl-D-glucal undergoes complete reaction with alcohols in benzene solution in the presence of boron trifluoride to give 4,6-di-OðOðAðEðDÞÞ −2,3-dideoxy-α-DÒÞ−EðE Þ−hex-hex-2-enopyranosyl as discussed by the authors, which can be used to prepare the known crystalline ethyl αglucoside easily and in greatly improved
Book ChapterDOI
Substitution-with-Allylic-Rearrangement Reactions of Glycal Derivatives
TL;DR: Glycals (or usually their O-substituted derivatives) are readily converted into 2,3-unsaturated glycosyl compounds with O-, C-, N-, S- or otherwise linked substituents at the anomeric position as discussed by the authors.
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