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Epoxides deoxy sugar from

The esters of deoxy compounds, used in Routes B and C, are prepared either from the products of reductive cleavage of epoxides, or from deoxy sugar derivatives synthesized by some other specific route. Sulfonyloxy substituents are eliminated in a basic medium or, as in the reaction of methyl 4,6-0-benzylidene-3-deoxy-2-0-p-tolylsulfonyl-a-D-aro6mo-hexo-side (75) (73), by heating the compound with soda-lime. In the carbo-... [Pg.103]

Deoxy-D-jcylo hexose 6-(dihydrogen phosphate) (21) has also been synthesized (2) the reaction sequence makes use of 3-deoxy l 2,5 6-di-O-isopropylidene D-galactofuranose (16), a compound that can be easily prepared from D-glucose (2, 60). The mono-isopropylidene derivative (17) formed by partial hydrolysis of the di-ketal is converted into the 6-tosylate (18) by reaction with one molar equivalent of p-toluenesulfonyl chloride. From this the epoxide (19) is formed by reaction with sodium methoxide. Treatment of the anhydro sugar with an aqueous solution of disodium hydrogen phosphate (26) leads to the 6-phosphate (20)... [Pg.80]

Ascarylose (94) and the (35) deuterium-labeled ascarylose were prepared starting from methyl a-L-rhamnopyranoside via the 2,3-anhydro sugar 120 (Scheme 34).204 Opening of the epoxide ring with lithium aluminum hydride in THF led selectively to the 3-deoxy derivative. If reduction was performed with lithium aluminum deuteride, the methyl (3S)-[32H]ascaryloside (3S)-[32H]119 was obtained. [Pg.181]

The 6-dcoxy-/J-D-c -c//hHohexofuranoside-5-ulose, a constituent of the sugar-cinnamate unit 234 of the antibiotic hygromycin, and several related analogues, have been synthesized from 6-deoxy-/J-D-glucofuranosides via a 2,3-epoxide and selective oxidation at C-5 with the Jones reagent.445... [Pg.269]

Mode of synthesis A. cyanohydrin, by way of 2-nmino-2-deoxy-aldonic acid B. scission of sugar derivative epoxide with ammonia C. interconversion of hexosamine series D. hemihydrogenation of a-amino nitrile466 E. rearrangement of ketosyl-amine F. Removal of last carbon atom of hexosamine G. Hydrazinolysis (with inversion) of 2-0-tosyl-pentose. 6 Physical constants taken from this reference. c Derivatives (only) isolated. [Pg.225]

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See also in sourсe #XX -- [ Pg.21 , Pg.152 , Pg.159 ]



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Deoxy sugars

Epoxides, sugar, deoxy sugars from

From epoxides

Sugar-epoxide

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