- Organoboron-catalyzed regio- and stereoselective formation of β-2-deoxyglycosidic linkages
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A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-sel
- Beale, Thomas M.,Moon, Patrick J.,Taylor, Mark S.
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supporting information
p. 3604 - 3607
(2014/07/21)
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- A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides
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A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.
- Balmond, Edward I.,Benito-Alifonso, David,Coe, Diane M.,Alder, Roger W.,McGarrigle, Eoghan M.,Galan, M. Carmen
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supporting information
p. 8190 - 8194
(2014/08/18)
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- Regio- and stereoselectivity of the addition of O-, S-, N-, and C-nucleophiles to the β vinyl oxirane derived from D-glucal
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6-O-Trityl- (1a) and 6-(O-benzyl)-substituted epoxide (1b) derived from D-glucal were examined in their addition reactions with O-, C-, N-, and S-nucleophiles. A 1,4-regio- and β-stereoselective or an anti 1,2-addition pathway is commonly observed dependi
- Di Bussolo, Valeria,Caselli, Micaela,Romano, Maria Rosaria,Pineschi, Mauro,Crotti, Paolo
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p. 8702 - 8708
(2007/10/03)
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- New stereoselective β-C-glycosidation by uncatalyzed 1,4-addition of organolithium reagents to a glycal-derived vinyl oxirane
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(Matrix presented) Epoxide 4 is generated in situ from D-glucal-derived hydroxy mesylate 3. Reaction of epoxide 4 with a series of alkyl- and aryllithium reagents affords 2,3-unsaturated β-C-glycosides with excellent 1,4-regioselectivity and complete ster
- Di Bussolo, Valeria,Caselli, Micaela,Pineschi, Mauro,Crotti, Paolo
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p. 2173 - 2176
(2007/10/03)
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- Strategy in oligosaccharide synthesis: An application to a concise total synthesis of the KH-1(adenocarcinoma) Antigen
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A concise and potentially practical synthesis of the title compound has been achieved. The route features a high degree of convergence and economy of synthetic operations. A key step is the concurrent introductory addition of three α-1-fucosyl residues at
- Deshpande, Prashant P.,Kim, Hyunjin M.,Zatorski, Andrzej,Park, Tae-Kyo,Ragupathi, Govindaswami,Livingston, Philip O.,Live, David,Danishefsky, Samuel J.
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p. 1600 - 1614
(2007/10/03)
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