Synthesis of the monosaccharide units of the O-specific polysaccharide of Shigella sonnei

Medgyes, A.; Farkas, Erzsébet; Lipták, András; Pozsgay, Vince

doi:10.1016/s0040-4020(97)00145-2

Cited by 73 publications

(50 citation statements)

References 37 publications

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“…[43,44] TEMPO oxidations with sodium hypochlorite as cooxidant have been described for a number of azido monosaccharides, affording the corresponding uronic acids in good yields. [13,45] The oxidation of azido disaccharides, however, has not yet been reported. The same is true for the TEMPO-catalyzed anodic oxidation of 1-azido carbohydrates.…”

Section: Preparation Of Methyl Glycosides Of Disaccharidesmentioning

confidence: 99%

TEMPO‐Mediated Anodic Oxidation of Methyl Glycosides and 1‐Methyl and 1‐Azido Disaccharides

Schämann

Schäfer

2002

Eur J Org Chem

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Methyl glycosides of L‐sorbopyranoside, D‐fructopyranoside, D‐glucosaminopyranoside, 2,3‐dehydro‐2,3‐dideoxyglucopyranoside, cellobiose, lactose, and maltose and the 1‐azido derivatives of glucose, cellobiose, lactose, and maltose have been converted into the corresponding uronic acids in moderate to excellent yields by TEMPO‐mediated anodic oxidation. The anode proves to be an advantageous alternative to other cooxidants in TEMPO+ oxidations of carbohydrates and is compatible with N‐acylamino and azido groups and with double bonds. The electrolyte, a carbonate buffer, can easily be removed with a cation‐exchange resin, a facile scale‐up by increasing the electrode area is possible. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Preparation Of Methyl Glycosides Of Disaccharidesmentioning

confidence: 99%

TEMPO‐Mediated Anodic Oxidation of Methyl Glycosides and 1‐Methyl and 1‐Azido Disaccharides

Schämann

Schäfer

2002

Eur J Org Chem

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“…4,6-Benzylidene-N-phthaloyl thioglucosamine (7) was obtained from -glucosamine in 40 % yield over eight steps on a 147-g scale. [26,27] Only a single chromatographic www.eurjoc.org purification was required in this sequence of reactions. Reductive opening of the benzylidene acetal in the next step was affected by treatment of 7 with trifluoroacetic acid (TFA) and triethylsilane (TES) to selectively provide key thioglycoside 6 in 85 % yield.…”

Section: Resultsmentioning

confidence: 99%

A Preparative Synthesis of Human Chitinase Fluorogenic Substrate (4′‐Deoxychitobiosyl)‐4‐methylumbelliferone

et al. 2010

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To meet the increasing clinical demand for the diagnostic agent (4′‐deoxychitobiosyl)‐4‐methylumbelliferone, a flexible and scalable route of synthesis is needed. In this paper such a route is presented. The key to the route is the use of a partially protected thiophenyl glucosamine as starting material for the preparation of both the reducing and nonreducing end building blocks of the 4′‐deoxychitobiose disaccharide.

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“…[28][29][30] For initial studies the easily accessible diisopropylidene aldehydo galactose 26 [19,31] was chosen. As 2-amino sugars the glucoamine derivatives 27 [32] and 28, obtained from 15 using a method according to Wong et al, [23] as well as the 2-amino-1,5-anhydro-glucitol 29 were selected. The linkage formation was easily done with sodium cyanoborohydride in aqueous methanol at pH 6 and room temperature.…”

Section: Reductive Aminationmentioning

confidence: 99%

“…Benzyl 2-acetamido-6-azido-2,6-dideoxy--glucopyranoside [43] (1.54 g, 4.58 mmol) was reacted according to general procedure 5 and the product purified by column chromatography [EE/MeOH The aldehyde 26 [19,31] (134 mg, 0.51 mmol) and amine 27 [32] (460 mg, 1.20 mmol) were stirred in methanol (5 mL) and reacted according to general procedure 3. After purification by column chromatography (PE/EE, 4:3) pure 32 (114 mg, 38 %) was isolated as a yellow syrup.…”

Section: Benzyl 2-acetamido-6-amino-26-dideoxy-d-glucopyranoside (31)mentioning

confidence: 99%

Synthesis of Novel Di‐ and Trisaccharide Mimetics with Non‐Glycosidic Amino Bridges

2007

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Synthesis of novel di‐ and trisaccharides using enzymatic glycosylation, Dess–Martin oxidation and reductive amination allows rapid access to the target structures. Thus, a novel class of glycomimetics was obtained having nitrogen inserted as bridging atom between two non‐anomeric positions. Novel di‐ and trisaccharide mimetics were designed using N‐acetylglucosamine as a basis structure. A third monosaccharide unit was attached via an unnatural sugar–sugar bond without participation of the anomeric center. Their synthesis, proceeding via oxidation, glycosylation and reductive amination, required only a few steps, thus allowing rapid access to the target structures. Generation of the novel pseudo‐disaccharide was achieved by Dess–Martin oxidation and a subsequent reductive amination. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Synthesis of the monosaccharide units of the O-specific polysaccharide of Shigella sonnei

Cited by 73 publications

References 37 publications

TEMPO‐Mediated Anodic Oxidation of Methyl Glycosides and 1‐Methyl and 1‐Azido Disaccharides

TEMPO‐Mediated Anodic Oxidation of Methyl Glycosides and 1‐Methyl and 1‐Azido Disaccharides

A Preparative Synthesis of Human Chitinase Fluorogenic Substrate (4′‐Deoxychitobiosyl)‐4‐methylumbelliferone

Synthesis of Novel Di‐ and Trisaccharide Mimetics with Non‐Glycosidic Amino Bridges

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