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Showing papers on "Glucal published in 2009"


Journal ArticleDOI
TL;DR: In this paper, an improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed, using ZnCl2 impregnated on activated alumina.

42 citations


Journal ArticleDOI
TL;DR: In the Rh(2)(OAc)(4)-catalyzed amidoglycosylation of glucal 3-carbamates, anomeric stereoselectivity and the extent of competing C3-H oxidation depend on the 4O and 6O protecting groups, which permits high alpha-anomer selectivity with further improvement in less polar solvents.

31 citations


Journal ArticleDOI
TL;DR: A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid, which acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides.

31 citations


Journal ArticleDOI
TL;DR: Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient temperature.

29 citations


Journal ArticleDOI
TL;DR: In this article, four chiral ruthenium carbonyl cluster complexes Ru3(μ-H)2(CO)9(L-2H) (1), Ru3μ-h)2 (CO)7(L2H)(dppm) (2) and Ru3mH2( CO)9 (L 2H)(3,4,6)-tri-O-benzyl-d-galactal (L) (4) were characterized.

15 citations


Journal ArticleDOI
TL;DR: In this paper, the first report on carbon-Ferrier rearrangement using isonitriles as nucleophiles was presented, and the use of FeCl3 makes this method simple, convenient and cost-effective.

15 citations


Patent
30 Dec 2009
TL;DR: In this article, a coumarin compound acidulated by glucal and application thereof is described, which has a structure showed in the right formular, wherein R is one of-H, -OH, -CH3, -OCH3 or ester group; and R1, R2, R3 and R4 are one of -H, OCH, -NH2 or glucal acid group.
Abstract: The invention relates to a coumarin compound acidulated by glucal and application thereof. The compound has a structure showed in the right formular, wherein R is one of-H, -OH, -CH3, -OCH3, -NH2 or ester group; and R1, R2, R3 and R4 are one of -H, -OH, -CH3, -SH, -OCH3, -NH2 or glucal acid group. The coumarin compound acidulated by the glucal has the activities of resisting arthritic and tumor.

5 citations


Journal ArticleDOI
TL;DR: In this paper, an improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed, using ZnCl2 impregnated on activated alumina.
Abstract: An improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 2,4,6-tri-O-acetyl- d -glucal to 2,3-unsaturated-O-glycosides with high α-selectivity.

4 citations




Journal ArticleDOI
TL;DR: In this article, a mild and efficient synthesis of pseudoglycosides using metal free (S )-camphorsulfonic acid was developed using a wide range of biologically active natural products, alcohols and thiols.
Abstract: A mild and efficient synthesis of pseudoglycosides has been developed using metal free ( S )-camphorsulfonic acid. ( S )-CSA acts as an excellent catalyst for conversion of 2,4,6-tri- O -acetyl- d -glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could be coupled with glucal to give the desired pseudoglycosides in good to excellent yields with exclusive α-stereoselectivity.

Journal ArticleDOI
TL;DR: In this paper, the authors explored the use of Hexafluoroisopropanol (HFIP) as an effective medium for the synthesis of 2,3-unsaturated glycosides through allylic rearrangement of 3,4,6-tri-O-acetyl glucal.
Abstract: Hexafluoroisopropanol (HFIP) is explored as an effective medium for the synthesis of 2,3-unsaturated glycosides through allylic rearrangement of 3,4,6-tri-O-acetyl glucal. This metal-free, exclusively solvent-promoted Ferrier glycosylation, affords products in good to excellent yields and with good α-selectivity.


Journal ArticleDOI
TL;DR: In this article, a one-pot transformation of d-glucal in the presence of nucleophiles leads to the formation of racemic α-substituted α-hydroxymethyl furfuryl derivatives, versatile synthons for biologically active molecules.
Abstract: Lewis acid mediated one-pot transformation of d-glucal in the presence of nucleophiles leads to the formation of racemic α-substituted α-hydroxymethyl furfuryl derivatives, versatile synthons for biologically active molecules. Transformations using O-, S-, C-, and N-nucleophiles could be achieved readily under mild and scalable conditions. Indium triflate proved to be the catalyst of choice in terms of conversion and regioselectivity.

Journal ArticleDOI
TL;DR: Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient temperature.
Abstract: Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient temperature. This methodology obviates the need for protecting and/or activating the C-3 hydroxyl group of glycals. The reaction works in equal ease with both 4,6-di-O-benzyl- d -glucal and 4,6-di-O-benzyl- d -galactal. The mildness of InCl3 makes this approach compatible for glycosyl acceptors with acid labile groups. The generality of the reaction has been demonstrated with a diversity of alcohols, phenols, and sugar nucleophiles.