Allitol, 2-deoxy

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°. 

This elegant synthesis also permits,94 by reduction of the nitrile 89, the synthesis of l-amino-2,5-anhydro-l-deoxy-D-allitol (91),... 

Substitution was also the major reaction in the deamination of l-amino-2,6-anhydro-l-deoxy-D-allitol 67and l-amino-2,6-anhydro-l,7-dideoxy-L-g(i/cero-L-ga(acfo-heptitol.168 The rearrangement product, a l,6-dideoxy-2-heptulose, was also isolated from the latter amine, the ratio of substitution to rearrangement being 1.6 1. 

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-... 

D-xylitol (59,81%), and 2- O -acetyl-1,4-anhydro-6-deoxy-3,5- 0-( 1,1,3,3-tetraiso-propyldisiloxan-l,3-diyl)-D-allitol (60,77%). The reported yields appeared to be independent of the anomeric configuration of the substrates, prepared in two steps from the corresponding glycofuranosyl azides, via the formamides. 

S.2.2 Synthesis from o-ribose D-Ribose has been used as a precursor for the synthesis of (-)-biopterin (1) by transformation to the 2,3-0-cyclohexylidene acetal 14 whose reaction with methylmagnesium iodide afforded 3,4-0-cyclohexylidene-6-deoxy-L-allitol... 

Tribenzoyl, N-ylc l-Acetamido-2,5-anhydro-3,4,6-tri-0-benzoyl-l-deoxy-D-allitol... 

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-l,5-anhydro-2,6-dideoxy-D-mannitol, A-149 l-Acetamido-2,5-anhydro-3,4,6-tri-0-benzoyl- 1-deoxy-D-allitol, A-122... 

Benzamido-2-deoxy-D-allitol, A-155 2-Benzamido-2-deoxy-D-allose, A-156... 

Amino-3,6-anhydro-2-deoxyglucitol D-form, A-128 2-Amino-l,6-anhydro-2-deoxyglucose p-D-Pyranose-/orm, A-132 2-Amino-1,5-anhydro-2-deoxy-4,6- O -isopropylidene-D-allitol, A-123 2-... 

Benzamido-2-deoxy-D-alIitoI, A-155 2-Benzamido-2-deoxy-D-alIose, A-156 2-Benzamido-2-deoxyglucose D-form, B-7 2-Benzamido-2-deoxy-3,4,6-tri-0 -methyl-D-glucopyranose, B-7 2-Benzamido-1,3,4,5,6-penta-O -benzoyl-D-allitol, A-155 2-Benzamido-3,4,6-tri-0-benzoyl-2-deoxy-a-D-glucopyranosyl bromide, A-223... 

Amino-2,5-anhydro-l,6-dideoxygludtol D-form, A-148 6-Amino-2,5-anhydro-l,6-dideoxygludtol D-form, A-148 l-Amino-2,5-anhydro-3,4,6-tri-0-benzoyl-l-deoxy-D-allitol, A-122 5-Amino-5-deoxyaltritol D-form N-Ac, A-162 5-Amino-5-deoxyaltritol L-/orm 4,5-Dibenzyl, 1,3-O-benzylidene,... 

Benzamido-1,3,4,5,6-penta- O -benzoyl-D-allitol, A-155 Benzyl 2,4-diamino-2,4-dideoxy-a-D-galactopyranoside, D-422 l-Deoxy-l-(methylamino)glucitol, 9CI, 8CI, A-214 l-Deoxy-l-[methyl(l-oxodecyl)amino]-D-glucitol, 9CI, A-214... 

Benzamido-l,3,4,5,6-penta-0-benzoyl-D-allitol, A-155 6- O -Benzoyl-1 -deoxy-D-galact i tol, D-123 l-0-Benzoyl-2,3 5,6-di-0-isopropylidene-D-allitol, A-75 6-O-Benzoyl-D-glucitol, G-247... 

Dibromo-2,6-dideoj -D-altrono-l,4-lactone can be converted into l-amino-3,6-anhydro-1 deoxy-D-allitol by reaction with sodium borol dride followed by aqueous ammonia. The same starting dibromide, on treatment with potasaum fluoride them aqueous ammonia, affords 3,6-dideoxy-3,6-imino-D-gluconic acid which can be reduced to l,4-dideoxy-l,4-iniuKM guIitol via the... 

Anhydro-l-deoxy-l-nitro-D-altritol and D-allitol derivatives, prepared by cyclization of corresponding 1-deoxy-l-nitro-D-altritol or D-allitol derivatives in dimethyl sulphoxide, undergo equilibration on heating in aqueous solvents via acyclic nitroalkene intermediates whereas the altro isomer (18) predominated with 3,4-O-isopropylidene derivatives, the alio isomer (19) was preferred for the monocyclic derivative. ... 

A synthesis of pseudouridine fct- and S" isomers) and of 5 -D-riboforanosyluridine has been reported. "Homouridine" and "homocytosine", having a methylene group inserted between N] of the pyrimidine and C] of the glycosyl group, were synthesized via the ureido derivative of l-deoxy-l mino-2,5-anhydro-D-allitol. ... 

Alditols, Cyclitols and Derivatives Thereof. - 2,5 3,4-Dianhydro-D-altritol, 2,5-aohydro-3,4-0-(l,2-ethanediyl)-D mannitol, pentaerythritol tetraacetate, ribitol tetraacetate, xylitol tetraacetate, D-arabinitol tetraacetate, D, L-arabinitol tetraacetate, 2,4 3,5-di-0-isopropylidene-D-mannitol, 2 hexa-O-acetyl-D-mannitol, allitol hexaacetate, D-mannitol hexaacetate, D, L-mannitol hexaacetate, D-iditol hexaacetate, D, L-iditol hexaacetate, D, L-glucitol hexaacetate, D, L-altritol hexaacetate, L-galacto-D-galacto-decitol (which is C2-symmetric), 5 6-0-benzyl-2,3-0-[(S)-caniphanylidene]-l,4,5-tris-0-pivaloyl-D-myo-inositol, 6D-3,6-di-0-benzyl-l-0-[(S)-camphanyl]-2-deoxy-2,2-difluoro-4,5-0-isopropylidene- y< -inositol, cyclopentane 28. ... 

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