Glucitol 2-amino-1,5-anhydro-2-deoxy

On deamination, 2-amino-l,5-anhydro-2-deoxy-l>mannitol gave l,5-anhydro-2-deoxy-D-eryf/iro-3-hexulose as the major product.54 The substitution product 1,5-anhydro-D-glucitol was formed to a small extent, and inversion again predominated, as with other axial amines (60, 72, and methyl 4-amino-4-deoxy-a-D-galactopyranoside) this is in accord with the predominant inversion of configuration reported for deamination, in water-rich media, of simple cyclohexyla-mines,154 and aminodecahydronaphthalenes39 in which the amino group is axial. As discussed previously (see p. 15), the extent of inversion can vary considerably with the nature of the solvent, and steric factors appear to be important in deaminations of per-O-acetyl amines (see pp. 37 and 49). 

Glucitol, 1-amino-l-deoxy-D-, 57 —, 2-amino-2-deoxy-n-, 57, 60 —, 1,4-anhydro-n-, 57 Glucofuranose, 1,2-0-isopropylidene-a-... 

The isolation of D-aroWno-hexulose phenylosazone from both 1,4-anhydro-D-mannitol and 1,5-anhydro-D-glucitol indicates that o-aroMno-hexosulose is among the reaction products. - Crude methyl D-glucofurano-sides in dilute sulfuric acid yield pyruvaldehyde, and 2-amino-2-deoxy-D-glucose hydrochloride suffers oxidative deamination. ... 

Nevertheless, compound 81 was definitely obtained later by deamination of 2-amino-l,6-anhydro-2-deoxy-j6-D-mannopyranose (103) with nitrous acid, and was identified by reduction to 2,5-anhydro-D-glucitol.366 An analogous deamination was performed with 2-amino-l,6-anhydro-2-deoxy-3-0-tosyl-/l-D-altropyranose to give, after detosylation, 2,5-anhydro-D-allose.361... 

Freeman, F, Roharge, K D, Stereoselectivity in the electrophile-mediated cyclization of 2,3,5-tri-O-benzyl-L2-dideoxy-D-arafano-hex-l-enitol. A stereocontrolled s)mthesis of l-amino-2,5-anhydro-3, 4,6-tri-O-benzyl-l-deoxy-D-glucitol, Carbohydr. Res., 171, 1-H, 1987. 

Amino-l,5-anhydro-6-deoxy-D-glucitol, prepared in standard reactions from D-glucose, has been used to prepare compounds (26)... 

Deamination of 2-amino-l,5-anhydro-2-deoxy-D-mannitol with nitrous acid gave principally l,5-anhydro-2-deoxy-D-e/ yt/fru-hex-3-ulose (68%), by migration of H-3, and some 2-deoxy-D-a/ a6/no-hexose (8%) and 1,5-anhydro-D-glucitol (6%). It was established that 2-deoxy-D-nrai>//in-hexose is formed via a hydride-shift mechanism, rather than by acid-catalysed hydration of D-glucal produced by an elimination pathway. 

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