Eine neue Klasse von Zuckerderivaten

Micheel, Fritz; Suckfüll, Fritz

doi:10.1002/jlac.19335020106

Cited by 22 publications

(8 citation statements)

References 10 publications

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“…Seven isomeric pent acetates of galactose are known products. These appear to be derivatives of alpha and beta galactofuranose [47,48], alpha and beta " galacto-pyranose [49, 50], alpha and beta d-galacto-septanose [51], and aldehydo-galactose [52]. The fact that these derivatives can be obtained lends credence to the concept that minute quantities of the corresponding modifications of the sugars are present in aqueous solutions.…”

mentioning

confidence: 84%

Bromine oxidation and mutarotation measurements of the alpha- and beta-aldoses

Isbell¹,

Pigman²

1937

J. RES. NATL. BUR. STAN.

106

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Rates of oxidation by bromine water, sp eci£c rotations, mutarotation coefficients, heats of activation, and other data are reported for a--ribose, l-ribose, a -l-rhamnose, a-lact ose, ,B-lactose, and ,B-maltose. The bromine oxidation measurements reveal that the equilibrium solutions are composed for the most part of the normal alpha and beta isomers. Small quantities of other modifications appear to be present in the solutions of arabinose, galactose, talose, and ribose. F undamental cha racteristics of the alpha and beta sugars which furnish t he basis for the changes in nomenclature previously suggest ed by Isbell are discussed. It is shown that the sugars which appear as beta modifications under the proposed classification are oxidized by bromine more rapidly than the alpha. CONTENTS

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mentioning

confidence: 84%

Bromine oxidation and mutarotation measurements of the alpha- and beta-aldoses

Isbell¹,

Pigman²

1937

J. RES. NATL. BUR. STAN.

106

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“…1,2 As in the synthesis of natural carbohydrates, attention has focused on the selective formation of glycosidic bonds involving the septanose residue. Glycosyl donor types include anomeric halides, 3 thioseptanosides, 4 and oxepinesdcyclic enol ethers. 5,6 Carbohydrate based oxepines have been key intermediates in our approach toward the synthesis of septanosides.…”

Section: Introductionmentioning

confidence: 99%

An oxepinone route to carbohydrate based oxepines

et al. 2009

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“…By a series of reactions a-and 0-1,2,3,4,5-penta-0-acetyl-D-galactoseptanose were prepared. The septanose structure was confirmed by conversion of the pentaacetate to a methyl tetra-0-methyl-D-galactoseptanoside \vhich, upon oxidation with nitric acid, gave tetra-0-methylmucic acid (17). In the present work the synthesis of a sugar derivative with nitrogen as the hetero atom in a seven-membered ring was attempted by a method analogous to that described by i\/Iicheel and Suc1;fiill (16).…”

Section: A T T E M P T E D Synti-iesis O F a Carbohydrate Containing mentioning

confidence: 69%

“…The synthesis of derivatives of seven-meinbered ring sugars or septanoses has beell achieved by iVIicheel et al (16)(17)(18). By a series of reactions a-and 0-1,2,3,4,5-penta-0-acetyl-D-galactoseptanose were prepared.…”

Section: A T T E M P T E D Synti-iesis O F a Carbohydrate Containing mentioning

confidence: 99%

Carbohydrates Containing Nitrogen in a Five-Membered Ring and an Attempted Synthesis of a Carbohydrate With Nitrogen in a Seven-Membered Ring

Szarek¹,

Jones²

1965

Can. J. Chem.

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Lead tetraacetate oxidation of 6-acetamido-6-deoxy-D-galactose ( I S ) yielded a syrup which was converted to a compound formulated as 4-acetamido-4-deoxy-l,2-0-i~o~ropylidene-Dthreofuranose (XII). The same syrup was obtained by alkaline degradation of the product of oxidation of 5-acetamido-5-deoxy-D-xylose diethyl dithioacetal (XVII) with peroxypropionic acid. Treatment of compound XI1 with p-toluenesulfonyl chloride yielded crystalline 4-acetamido-4-deoxy-1,2-0-isopropylidene-3--p-tolysufo1yl-~-threofuranose (XIII).Dernercaptalation of 6-acetamido-2,3,4,5-tetra-0-acetyl-6-deoy-~-gaactose diethyl dithioacetal (SS) with mercuric chloride and cadmium carbonate ~n aqueous acetone did not yield a nitrogen-containing septanose ring but an acyclic derivative. CARBOHYDRATES CONTAINIXG NITROGEZV IN A FIVE-MEMBERED R I N GIn a previous paper (I) froin this laboratory the synthesis of methyl 4-acetamido-4-deoxy-L-erythrofuranoside (I), the first example of a sugar with nitrogen in a fiveinenlbered ring, was described. Very shortly after this announcement, Hanessian and Haslcell (2) reported that they had obtained syrupy 4-acetamido-4-deoxy-L-erythrofuranose by the alkaline degradation of 5-acetamido-5-deoxy-L-arabinose diethylsulfonal. In the same paper Hanessian and Hasltell reported the preparation of a novel sugar derivative, 4-amino-4-deoxy-D-erythronolactain (11). In the present publication we describe the synthesis by two different routes of derivatives of 4-acetamido-4-deoxy-Dthreofuranose (XI). 1,2;3,4-Di-0-isopropylidene-a-~-ga1actopyran0se (IV) (3) was prepared from D-galactose (111) and treated with p-toluenesuIfony1 chloride in pyridine to give 1,2;3,4-di-O-isopropylidene-6-0-p-to~ylsulfonyl-a-~-galactop~ranose (V) (4). Con~pound V reacted with sodium azide in N,N-dimethylformamide t o afford a homogeneous pale yellow oil, the infrared spectrunl of which showed the highly characteristic azide group absorption a t 2 100 cm-I but no aromatic ring and sulfonate group absorptions. The new substance is therefore G-azido-G-deoxy-1,2;3,4-di-0-isopropylidene-a-~-galactopyranose (VI). This derivative could be reduced to 6-ai1~ino-6-deoxy-1,2;3,4-di-O-isoprop~~lidene-a-~-galactopyranose (VII) ( 5 ) by merely stirring it with a n excess of Raney nickel, a procedure described by Wolfrom et al. (6). Treatment of compound VII with acetic anhydride in pyridine afforded a glass which gave a negative ninhydrin reaction. The glassy product 'Preset~ted i n part at the Intertzational Synzposiunz on Carbohydrate Clzeftzistry, Miinster, July 13-17,1964. 2Present address:

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Eine neue Klasse von Zuckerderivaten

Cited by 22 publications

References 10 publications

Bromine oxidation and mutarotation measurements of the alpha- and beta-aldoses

Bromine oxidation and mutarotation measurements of the alpha- and beta-aldoses

An oxepinone route to carbohydrate based oxepines

Carbohydrates Containing Nitrogen in a Five-Membered Ring and an Attempted Synthesis of a Carbohydrate With Nitrogen in a Seven-Membered Ring

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