6-Desoxy-D-glucose

Mehltretter gelang es, D-Glucose mit Platin/Kohle-Katalysator bei erhohter Temperatur zu D-Glucarsaure zu oxydieren Analog erhalt man aus 2-Desoxy-D-glucose 2-Desoxy-D-glucarsaure, die als Dilacton isoliert wurde... 

Heparin is a heteropolysaccharide whose chains consist of alternating derivatives of 2-amino-2-desoxy-D-glucose and uronic acid linked together via 1 - 4 glycoside bonds 12). 

D-xylose,30 60 116 2-desoxy-D-glucose,3,6, 6 11, 121 3-methyl-2-desoxy-D-glu-cose,122 3,4,6-trimethyJ-2-desoxy-D-glucose,126 2-desoxy-D-galactose,124-128... 

The method was used successfully initially for the preparation of 2-desoxy-D-glucose.4 D-Arabinose was treated with nitromethane in the presence of sodium methoxide and gave a mixture of 1-nitro-l-desoxy-D-mannitol (XXXV) and 1-nitro-l-desoxy-D-glucitol (XXXVI). The mixture was not separated, but was acetylated and subsequently treated with bicarbonate to convert it into D-arabo-3,4,5,6-tetraacetoxy-1 -nitro-... 

Recently D-arabinose was combined with nitromethane which had been rendered radioactive by the incorporation of the C14 isotope,166 and so there is a possibility of preparing radioactive 2-desoxy-D-glucose. 

Desoxysugars are characterized by their ease of conversion to O-glycosides. When 2-desoxy-D-glucose is treated for 15 minutes with... 

Other methods have been used to prepare O-glycosides of desoxysugars. Bergmann and his coworkers118 converted tetrabenzoyl-2-desoxy-D-glucose into l-bromo-tribenzoyl-2-desoxy-D-glucose by the standard procedure. This latter compound, when treated with methanol in the presence of silver carbonate, afforded after debenzoylation, methyl 2-desoxy-/3-D-glucoside. 

Simple Aromatic Amines.—Crystalline anilides of 2-desoxy-D-galac-tose,223 2-desoxy-D-glucose,120 223 2-desoxy-D-xylose,60 and 2-desoxy-D-158 and -L-ribose112 have been obtained by the usual method of synthesis of... 

Reaction of l-bromo-3,4,6-triacetyl-2-desoxy-D-glucose with 5,6-dimethylbenzimidazole silver in hot xylene gave a non-crystalline mixture of a- and /3-isomers which could not be resolved by fractionation pro-... 

The addition of water to the trimethyl ether of D-glucal led to the formation of the 3,4,6-trimethyl ether of 2-desoxy-D-glucose.6... 

In the six-carbon series,8 the selective hydrogenation of d-ardbo-tetraacetoxy-l-nitrohexene-1 gave crystalline l-nitro-l,2-didesoxy-D-aro o-hexitol tetraacetate in 79 percent yield. This product, on de-acety-lation followed by the Nef reaction, then gave D-ara6o-2-desoxyhexose ( 2-desoxy-D-glucose ), isolated as the benzylphenylhydrazone,60 in high yield. 

Cytidin- -dimethylester XII/2, 272 Cytidin-5 - -morpholid XII/2, 402 Cytidin- -propylester XII/2, 272 -decylamid-dichlorid XII/2, 385 -decylamid-diphenylester XII/2, 435 -decylester XII/2, 179 E2, 500, 561 -decylester-dichlorid XII/2, 213f. Desoxy-adenosin-5 - XII/2, 207 Desoxy-cytidin-3 - XII/2, 180 Desoxy-cytidin-5 - -morpholid XII/2, 402 2-Desoxy-3,4-di-0-benzoyl-D-ribose-dimethyl-acetal-5- -diphenylester XII/2, 194 -6-(desoxy-D-gluconsaureester) XII/2, 209 2-Desoxy-D-glucose-6- XII/2, 194... 

Scheme 4S. Potato phosphorylase-catalyzed synthesis of 2-desoxy-D-glucose 1-phosphate 135...

Wolfrom and Conigliaro4 found that S-ethyl trifluorothioacetate selectively acylates the amino group of 2-amino-2-desoxy-D-glucose (methanolic sodium methoxide, 24 hours, room temperature, 73% yield). They used this protective group in the synthesis of purine nucleosides. The group was removed by means of methanolic ammonia. (Note that purine nucleosides are unstable to acid.)... 

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