Talitol, 1,5-anhydro

On treatment with concentrated halogen acids, certain hexitols yield 1,6-dideoxy-l,6-dihalo compounds. The structure of the compound so obtained from galactitol, first reported by Bouchardat,404 was later verified by synthesis.405 Allitol is transformed406 into 1,4-anhydro-6-chloro-6-deoxy-DL-allitol and l,4-anhydro-5,6-dichloro-5,6-dideoxy-DL-talitol on treatment with fuming hydrochloric acid at 100°. 

Anhydromannitol, 2,5-anhydro-3-O-methyl-mannitol, 2,5-anhydro-talitol 5% SE-30 170-190 amino sugars + HN02 564... 

DL-galactonic acid (39). 1,4-Anhydro-DL-talitol (3,6-anhydro-DL-altritol) (40) gave 2-0-(carboxymethyl)-DL-threaric acid (41) and 1,4-anhydro-D-mannitol (42) gave 2-0-(carboxymethyl)erythraric acid (43). 

Di-O-mesyl-D-mannitol (46) can be converted under acidic conditions (Dowex 50W-X2 cation-exchange resin) by way of 1,4-anhydro-3-0-mesyl-D-talitol (47) into D-isoidide (49) in almost quantitative yield. On using triethylamine - water, 2,3 4,5-dianhydro-D-iditol (48) is formed from this, on treatment with an acid ion-exchanger, D-isoidide (49) is formed in only 20% yield (see Scheme 7). From these observations, it was decided5 7,98 that the 2,3 4,5-dianhydro isomer 48 cannot be an intermediate in the conversion of 46 into 49. Similar results were found for the reaction of 46 or 3,4-di-O-p-tolylsulfonyl-D-mannitol (p-CH3C6H4S02- instead of CH3S02-in 46) with barium methoxide in methanol.99... 

The isocyanide method of reduction has been applied successfully for preparing a series of diversely protected 1,4-anhydroalditols 188 l,4-anhydro-5-O-tert-butyldimethylsilyl-2,3-0-isopropylidene-D-ribitol (56, 81%), l,4-anhydro-5-0-terf-butyldimethylsilyl-6-deoxy-2,3-0-isopropylidene-D-allitol (57,87%) and -l-talitol (58,87%), 1,4-anhydro-2- 0-rert-butyldimethylsilyl-3,5- 0 -isopropylidene-... 

On hydrolysis with acid, 5-acetamido-5-deoxy-L-gulofuranose (see Section III, 2 p. 176) gives 5-hydroxy-2-pyridinemethanol (46). As regards their stability in the presence of acids, it is not yet clear whether 5-amino-5,6-dideoxyaldohexoses behave like 5-amino-5-deoxyaldohexoses or like 5-amino-5-deoxyaldopentoses. By reductive ring-enlargement, 5-azido-5,6-dideoxy-L-talofuranose (see Section III, 2 p. 177) gives l-amino-l,5-anhydro-l,6-dideoxy-L-talitol, whose... 

Tagatose, d-conformation of, 32 infrared spectrum of, 39 Talitol, 1 -amino-1,5-anhydro-1,6-dideoxy-L-, 138... 

J. Defaye, Desamination nitreuse de la D-galactosamine. Preparation des 2,5-anhydro-D-talose et 2,5-anhydro-D-talitol, Bull. Soc. Chim. Fr. p. 999 (1964). 

Deamination of N-deacetylated glycosamino-glycans followed by sodium borodeuteride reduction led to pseudo-disaccharides of 2,5-anhydro-D-mannitol or -D-talitol (from D-glucosamine and D-galact-osamine residues respectively) with attached glucuronic acid,... 

O-Isopropylidene, l>l,6-di-Ac 1-Aceta-mido-6-0-acetyl-2,5-anhydro-l-deoxy-3,4-O-isopropylidene-D-talitol [110911-40-5]... 

Acetamido-l,5-anhydro-2-deoxy-D-mannitol, A-141 2-Acetamido-l,5-anhydro-2-deoxy-D-talitol, A-144... 

Acetamido-1,5-anhydro-2-deoxy-D-mannitol, A-141 2-Acetamido-1,5-anhydro-2-deoxy-i>talitol. A-144 2-Acetamido-l,5-anhydro-3,4-di-0-benzyl-2-deoxy-D-mannitol, A-141 2-Acetamido-l,5-anhydro-3,4-di-0-benzyl-2,6-dideoxy-D-mannitol, A-149 2-Acetamido-1,5-anhydro-2,6-dideoxy-D-mannitol, A-149 2-Acetamido-3,4,6-tri-0-acetyl-l,5-anhydro-2-deoxy-D-talitol, A-144... 

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