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2-acetamido-tetra-0-acetyl-2-deoxy

Similar /3-eliminations occur with 2-acylamino-2-deoxyaldoses, and an enamine derivative believed to be 2-acetamido-2,3-dideoxy-D-erj/after treatment of 2-acetamido-tetra-O-acetyl-2-deoxy-/3-D-glucose under basic conditions (91) was also thought to be the first product formed in the Morgan-Elson test for 2-acetamido-2-deoxyhexoses. < >> Although furan compounds are ultimately formed in this reaction, there would seem to be small reason to doubt that a single elimination from a simple derivative of n-glucose would give an unsaturated, pyranoid product. [Pg.108]

A-Acetyl-9-deoxy-9-fluoroneuraminic acid (591) was prepared by treatment of a protected 6-hydroxyl precursor with A, A-diethylaminosulfur trifluoride (DAST) or through condensation of 2-acetamido-2,6-dideoxy-6-fluoro-D-mannopyranose with potassium di(/ >r/-butyl) oxaloacetate. Compound 591 is a substrate for cytidine monophosphate (CMP)-sialic acid synthetase, giving rise to CMP-5-A-acetyl-9-deoxy-9-fluoroneuraminic acid, which is cytotoxic against tumor cells. 5-A-Acetyl-3-fluoroneuraminic acids 592-594 were prepared through fluorine (or acetyl hypofluorite) addition (in AcOH) to methyl 5-acetamido-4,7,8,9-tetra-0-acetyI-2,6-anhy-dro-2,3,5-trideoxy-D- /ycm>D- a/arto-non-2-enopyranosate. Compound 592 was found to be a potent neuraminidase inhibitor. [Pg.210]

The disaccharide derivative 0-(2,3,4,6-tetra-0-acetyl-/ -D-galactopy-ranosyl)-(l— 3)-0-(2-acetamido-6-0-benzoyl-2-deoxy-/ -D-glucopyran-osyl)-(l— 3)-N-(benzyloxycarbonyl)-L-serine methylamide (192) was prepared by condensation of 3-0-(2-acetamido-2-deoxy-6-0-benzoyl-/ -D-glucopyranosyl)-N-(benzyloxycarbonyl)-L-serine methylamide (191) with tetra-O-acetyl-a-D-galactopyranosyl bromide147 (110) under the conditions of the Helferich-Wedemeyer procedure. Treatment of 192 with methylamine in methanol at 0° gave89 193. [Pg.174]

D-Galactopyranosyl-(l- 3)-0-(2-acetamido-2-deoxy-a-D-galactopyranosyI) (2, 3, 4, 6 -tetra-0-acetyl-4,6-di-0-acetyl),... [Pg.200]

SCHEME 13. Preparation of methyl 2-acetamido-3,4,5,7-tetra-0-acetyl-2-deoxy-a-D-g/yc< ro-D-f(fo-sep-tanoside (68). [Pg.136]

V"-Fluoren-9-ylmethoxycarbonyl-3-0- 2-acetamido-2-deoxy-3,4-0-isopropyKdene-6-0-[methyl(5-acet-amido-4,7,8,9-tetra-0-acetyl-3,5,-dideoxy-D-glycero-a-galacto-2-nonulopyranosyl)onate]-a-D-galacto-pyranosylJ-L-threonme Benzyl Ester (84) 11251... [Pg.265]

Nonphysiological compounds have also been described as influencing the overall metabolism of sialic acid. Administration of ethanol (2 g/kg) to rats significantly decreases the sialic acid content of brain tissue.246 Convulsions induced by pentylenetetrazole (6,7,8,9-tetrahy-dro-5/f-tetrazoloazepine) are accompanied by a diminution in the rate of biosynthesis of polysialogangliosicles GT, and GQn, in rat brain.227 Such ManNAc analogs as 2-acetamido-l,3,4,6-tetra-0-acetyl-2-deoxy-D-mannopyranose or the 2-(trifluoroacetamido) derivative lead to a marked lowering of the incorporation of radioactivity from labelled ManNAc into glycoconjugate sialic acids of murine, erythroleukemia (Friend) cells.247... [Pg.181]

Wohl3,4 extended this reaction to 2,3,4,5,6-penta-O-acetyl-D-galac-tononitrile (3) and to 2,3,4,5-tetra-O-acetyl-L-arabinononitrile (5), which led to l,l-bis(acetamido)-l-deoxy-D-lyxitol (4) and 1,1-bis-(acetamido)-l-deoxy-L-erythritol (6), respectively. [Pg.82]


See other pages where 2-acetamido-tetra-0-acetyl-2-deoxy is mentioned: [Pg.87]    [Pg.136]    [Pg.87]    [Pg.169]    [Pg.171]    [Pg.201]    [Pg.518]    [Pg.136]    [Pg.60]    [Pg.105]    [Pg.139]    [Pg.146]    [Pg.151]    [Pg.155]    [Pg.310]    [Pg.315]    [Pg.290]    [Pg.135]    [Pg.293]    [Pg.294]    [Pg.281]    [Pg.281]    [Pg.35]    [Pg.53]    [Pg.241]    [Pg.22]    [Pg.70]    [Pg.111]    [Pg.128]    [Pg.231]   


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Glucopyranoside, 2-acetamido-3,4,6-triO - acetyl - 2 - deoxy -a-D - glucopyranosyl 2,3,4,6-tetra-Oacetyl oxidn

Glucopyranoside, 2-acetamido-3,4,6-triO - acetyl - 2 - deoxy -a-D - glucopyranosyl 2,3,4,6-tetra-Oacetyl reaction with

Glucopyranoside, 2-acetamido-3,4,6-triO - acetyl - 2 - deoxy -a-D - glucopyranosyl 2,3,4,6-tetra-Oacetyl reaction with alkali

Glucopyranosyl 2-acetamido-tetra-0-acetyl-2-deoxy

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