Showing papers on "Glucal published in 2002"
TL;DR: 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.
46 citations
TL;DR: In this paper, short synthetic routes to protected derivatives of 2-amino-2-deoxy-α-d -glucopyranosyl-(1→6)- d -myo-inositol are described.
32 citations
TL;DR: Microwave irradiation of a mixture of tri-O -acetyl-d -glucal 1 and an appropriate alcohol 2a-f, in the presence of Montmorillonite K-10 as a catalyst, provided unsaturated glycosides 3a- f in much shorter time and in yields comparable with conventional heating.
32 citations
TL;DR: Tri-O-acetyl imino glucal 2 is readily made and shown to undergo a variety of Lewis acid mediated carbon-carbon bond forming reactions at C-1 of the piperidine nucleus.
31 citations
TL;DR: Chiral medium-sized monocyclic ethers corresponding to the D-, E-, F-, and I-ring parts of ciguatoxin have been synthesized from tri-O-acetyl-D-glucal through a common synthetic route involving ring-closing olefin metathesis as mentioned in this paper.
Abstract: Chiral medium-sized monocyclic ethers corresponding to the D-, E-, F-, and I-ring parts of ciguatoxin have been synthesized from tri-O-acetyl-D-glucal through a common synthetic route involving ring-closing olefin metathesis.
28 citations
TL;DR: This work prepared two novel templates suitable for use in combinatorial chemistry strategies for the construction of a number of interesting beta-lactam motifs using a diastereoselective Ferrier reaction of a glucuronic acid glucal.
27 citations
TL;DR: The reaction of the vinyl oxirane 1 derived from d-glucal with a series of O-nucleophiles affords the corresponding 2-unsaturated β-O-glycosides in a completely stereoselective way (syn 1,4-addition pathway) as mentioned in this paper.
27 citations
TL;DR: Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars.
23 citations
TL;DR: Syntheses of higher acyclic nitrogen containing deoxy sugar derivatives via nitroaldol reaction of different nitroalkanes with 2,3-dideoxy-alpha,beta-unsaturated aldehydo sugars obtained from glycals namely acetylated glucal and galactal and their in vitro antimycobacterial activity are presented.
19 citations
TL;DR: In this article, the synthesis of new enantiomerically pure γ-lactams from d -glucal and d -galactal as starting materials is described.
17 citations
TL;DR: In this article, a facile synthesis of electron-rich cage molecules based on the Ferrier allylic rearrangement of d -glucal followed by Glaser oxidative homocoupling of bridged disaccharides afforded two new 22 and 23-membered ring systems, which could be characterized by X-ray diffraction.
TL;DR: Some N-substituted-3-azabicyclo[3.3.0]octen-7-one derivatives have been synthesized in an enantiomerically pure form starting from tri-O-acetyl-D-glucal via intramolecular Pauson-Khand (IPK) cycloaddition.
Abstract: Some N-substituted-3-azabicyclo[3.3.0]octen-7-one derivatives have been synthesized in an enantiomerically pure form starting from tri-O-acetyl-D-glucal via intramolecular Pauson-Khand (IPK) cycloaddition.
TL;DR: In this paper, β-C-Glycosides were synthesized in one-pot experiments using the following sequence of four reactions: (i) addition of p-TolSCl to an α-methoxyalkene, (ii) generation of the episulfonium ion from...
TL;DR: Under the same conditions, the use of 2-methylthiophene, furan, 2-methylfuran, or N-methylpyrrole yields (2S,3R,4R,5S)-1,3,4-tribenzyloxy-6,6-diheteroaryl-5-(p-tolylthio)-2-hexanoles.
TL;DR: Cyclopropanation of 4,6-O-benzylidene-D-glucal, followed by tributylstannyl radical-mediated regioselective ring opening of the 1,2-cyclopropano sugar led to a 2, 6-anhydro-1-deoxyheptose, (a "methyl C-beta- D-glycoside").
TL;DR: Microwave irradiation of a mixture of tri-O -acetyl-d -glucal 1 and an appropriate alcohol 2a-f, in the presence of Montmorillonite K-10 as a catalyst, provided unsaturated glycosides 3a- f in much shorter time and in yields comparable with conventional heating as mentioned in this paper.
Abstract: Microwave irradiation of a mixture of tri- O -acetyl- d -glucal 1 and an appropriate alcohol 2a – f , in the presence of Montmorillonite K-10 as a catalyst, provided unsaturated glycosides 3a – f in much shorter time and in yields comparable with conventional heating.
TL;DR: In this article, the synthesis of new enantiomerically pure γ-lactams from d -glucal and d -galactal as starting materials is described.
Abstract: Syntheses of new enantiomerically pure γ-lactams 4a , b and δ-lactams 5a , b from d -glucal ( 3a ) and d -galactal ( 3b ) as starting materials are described.
TL;DR: In this paper, 1,6:2,3-Dianhydro-β-d -glucopyranose and its 3-alkylated derivatives were prepared from d-glucal in one pot with overall isolated yields of 60-70%.
Abstract: 1,6:2,3-Dianhydro-β- d -glucopyranose and its 3-alkylated derivatives were prepared from d -glucal in one pot with overall isolated yields of 60–70%, and these Cerny epoxides were further conveniently converted to selectively blocked 2-azido-2-deoxy-β- d -glucopyranose derivatives by azido opening of the epoxide ring.
TL;DR: Chiral medium-sized monocyclic ethers corresponding to the D-, E-, F-, and I-ring parts of ciguatoxin have been synthesized from tri-O-acetyl-D-glucal through a common synthetic route involving ring-closing olefin metathesis as discussed by the authors.
Abstract: Chiral medium-sized monocyclic ethers corresponding to the D-, E-, F-, and I-ring parts of ciguatoxin have been synthesized from tri-O-acetyl-D-glucal through a common synthetic route involving ring-closing olefin metathesis.
TL;DR: Tri-O-acetyl imino glucal 2 is readily made and shown to undergo a variety of Lewis acid mediated carbon-carbon bond forming reactions at C-1 of the piperidine nucleus.
Abstract: Tri-O-acetyl imino glucal 2 is readily made and shown to
undergo a variety of Lewis acid mediated carbon–carbon bond forming reactions
at C-1 of the piperidine nucleus. In all the reactions studied, the β-anomer
is predominant.