Process for producing carbon-reduced aldose compounds

Details Process for producing carbon-reduced aldose compounds Process for producing carbon-reduced aldose compounds

C - Chemistry, Metallurgy

07

C

C07C 323/12 (2006.01) C07C 317/18 (2006.01) C07H 3/02 (2006.01) C07H 3/08 (2006.01)

Patent

CA 2592598

A process by which 5-deoxy-L-arabinose, which is important as a material for the production of saproterin, a useful therapeutic agent for atypical hyperphenylalaninemia, can be industrially and efficiently produced even with a simple production apparatus. The process for 5-deoxy-L-arabinose production is characterized by reacting L-rhamnose with a C11-16 linear alkyl mercaptan compound in the presence of an acid catalyst to yield an L-rhamnose di(alkyl mercaptal), subsequently subjecting the resultant compound to an oxidation reaction to obtain a sulfonyl derivative, and then subjecting it to a carbon diminution reaction. This production process is applicable to a process for the production of a compound formed by removing one carbon atom from another aldol compound. Thus, the process is one for producing carbon-diminished compounds of general aldoses.

L'invention concerne un procédé permettant une production industrielle et efficace, même avec un appareillage de production simple, du 5-désoxy-L-arabinose, lequel est important en tant que matériau destiné à la production de la saprotérine, agent thérapeutique utile pour une hyperphénylalaninémie atypique. Le procédé destiné à la production du 5-désoxy-L-arabinose est caractérisé par la réaction de L-rhamnose avec un composé mercaptan à chaîne alkyle linéaire en C<SUB>11</SUB> à C<SUB>16</SUB> en présence d'un catalyseur acide pour donner un L-rhamnose di(alkylmercaptal), suivie d'une oxydation du composé résultant pour obtenir un dérivé sulfonyle et d'une réaction de diminution du nombre d'atomes de carbone. Ce procédé de production est applicable à un procédé de production d'un composé formé en retirant un atome de carbone d'un autre composé aldol. Ainsi, le procédé est destiné à produire des composés de type aldose général avec une diminution du nombre d'atomes de carbone.

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