- PROCESSES FOR PREPARING ALDARIC, ALDONIC, AND URONIC ACIDS
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Various processes for preparing aldaric acids, aldonic acids, uronic acids, and/or lactone(s) thereof are described. For example, processes for preparing a C2-C7 aldaric acid and/or lactone(s) thereof by the catalytic oxidation of a C2-C7 aldonic acid and/or lactone(s) thereof and/or a C2-C7 aldose are described.
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Paragraph 0092-0094
(2021/05/29)
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- Deoxyiminoalditols from aldonolactones; I. Preparation of 1,4-dideoxy-1,4-iminohexitols with D- and L-allo and D- and L-talo configuration: Potential glycosidase inhibitors
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1,4-Dideoxy-1,4-iminohexitols were prepared by a convenient two-step reaction from 2,6-dibromo-2,6-dideoxyhexono-1,4-lactones by treatment with aqueous ammonia and subsequent reduction of the carboxy function with sodium borohydride. By interchange of the reactions, the dibromolactones were reduced to 2,6-dibromohexitols, which by reaction with aqueous ammonia yielded the same imino compounds. Thus, from 2,6-dibromo-2,6-dideoxy-D-mannono- (1) and -D-glucono-1,4-lactone (9) the 1,4-dideoxy-1,4-imino-L-allitol (6) and -D-talitol (14) were prepared, respectively. These two compounds were also obtained from 2,6-dibromo-2,6-dideoxy-D-mannitol (5) and -D-glucitol (13), respectively, by reaction with aqueous ammonia. The enantiomeric 1,4-dideoxy-1,4-imino-D-allitol (18) and -L-talitol (22) were prepared similarly from the new 2,6-dibromo-2,6-dideoxy-L-mannono- (16) and -L-glucono-1,4-lactone (20), via the dibromo-L-hexitols 17 and 21, respectively. The ring closure of the dibromo compounds with ammonia has been shown to proceed via epoxides.
- Lundt,Madsen
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p. 714 - 720
(2007/10/02)
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