- Synthesis of 5,6-dimodified open-chain D-fructose derivatives and their properties as substrates of bacterial polyol dehydrogenase
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5-Deoxy-5-fluoro-D-xylulose as well as a range of new 5,6-dimodified open-chain analogues of D-fructose, namely the 5,6-diazido-5,6-dideoxy, 6-azido-5,6-dideoxy, 6-azido-5,6-dideoxy-5-fluoro, 5,6-dideoxy-5-fluoro, 5,6-dideoxy-6-fluoro and 5,6-dideoxy-5,6-
- Hadwiger, Philipp,Mayr, Peter,Nidetzky, Bernd,Stuetz, Arnold E.,Tauss, Andreas
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p. 607 - 620
(2007/10/03)
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- Synthesis of a 1-oxacephem structurally related to clavulanic acid from D-glucuronolactone
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[2+2]Cycloaddition of chlorosulfonyl isocyanate to 3-O-vinyl ethers derived from D-glucose and D-glucuronolactone proceeded with an excellent stereoselectivity to provide azetidin-2 ones with (R) configuration at C-4'. Intramolecular N-alkylation afforded 1-oxabicyclic β-lactams having six- or seven-membered ring fused to the four-membered one.
- Furman, Bartlomiej,Molotov, Sergiej,Thuermer, Rene,Kaluza, Zbigniew,Voelter, Wolfgang,Chmielewski, Marek
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p. 5883 - 5890
(2007/10/03)
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- Control of regioselectivity in reactions of dialkylstannylene acetals. Part I. A dramatic reversal of regioselectivity in mono-p-toluenesulfonation reactions
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The regioselectivities of p-toluenesulfonation reactions of dialkylstannylene acetals obtained from a number of carbohydrate-derived terminal 1,2-diols in the absence of added nucleophiles have been explored as functions of the carbohydrate structure, the
- Kong, Xianqi,Grindley, T. Bruce
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p. 2396 - 2404
(2007/10/02)
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- SYNTHESIS OF SOME ARYL 2,3,4,6-TETRA-O-ACETYL-L-IDOPYRANOSIDES AND OF 4-METHYLCOUMARIN-7-YL α-L-IDOPYRANOSIDURONIC ACID
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Several routes for synthesis of 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-β-L-idofuranose have been evaluated.Previously described routes, which involved selective sulphonylation, were not reproducible on a 100-g scale.To overcome this difficulty, a new variation was developed, involving complete tosylation of 1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone followed by reduction and acetylation.The idofuranose derivative was converted into the desired 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose via 1,6-anhydro-β-L-idopyranose.Fusion of 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose with 4-nitrophenol, 1- or 2-naphtol, or 4-methylcoumarin-7-ol, using freshly fused zinc chloride as catalyst, gave an anomeric mixture of glycosides, with the α anomer being preponderant.The major 4-methylcoumarin-7-yl glycoside was deacylated and converted, by catalytic oxidation, into 4-methylcoumarin-7-yl α-L-idopyranosiduronic acid, fluorogenic substrate for α-L-iduronidase.
- Baggett, Neil,Samra, Amarjit K.,Smithson, Alan
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- A novel synthesis of 5-thio-D-glucose
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A shorter synthesis of 5-thio-D-glucose is described in 8 steps from commercially available D-glucofurano-3,6-lactone.
- Driguez,Henrissat
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p. 5061 - 5062
(2007/10/02)
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