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Process for producing carbon-diminished aldose compound

A manufacturing method and compound technology, applied in the field of 5-deoxygenation, which is useful for synthesizing intermediates, can solve problems such as air pollution and deterioration of the operating environment, and achieve high industrial applicability

Inactive Publication Date: 2007-12-19
ASUBIO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it not only deteriorates the operating environment, but also causes air pollution in the surrounding area, and cannot be manufactured by general manufacturing facilities. In order to prevent environmental pollution, special deodorization and deodorization devices must be used

Method used

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  • Process for producing carbon-diminished aldose compound
  • Process for producing carbon-diminished aldose compound
  • Process for producing carbon-diminished aldose compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] Example 1: Production of L-rhamnose bis(dodecyl)thioacetal (XVI)

[0121] [chemical formula 17]

[0122]

[0123] Heat and dissolve 4.00g (22mmol) L-rhamnose (V) hydrate in 20mL dioxane, and add 8.89g (44mmol) n-dodecylmercaptan 4N hydrochloric acid little by little under stirring at room temperature / dioxane solution. After the dropwise addition, the reaction solution was transparent, and white crystals were deposited while the reaction was proceeding. Stir at room temperature for 12 hours, filter the precipitated white crystals, wash with ether and dry to obtain 9.00 g (yield 75%) of L-rhamnose bis(dodecyl) thiol (XVI) in the form of white crystals. ). This product can be directly put into the next reaction without purification, and colorless needle crystals can be obtained by recrystallization from dioxane.

[0124] Melting point: 111-112°C

[0125] IR spectrum (cm -1 ) 2917, 2850, 1467, 1064, 972, 894, 721, 613, 507, 422.

[0126] NMR spectrum (DMSO-D 6 ...

Embodiment 2

[0127] Example 2: 1,1-bis(dodecylsulfonyl)-1-mannose-2,3,4,5-tetrahydrohexane (XVII) manufacture

[0128] [chemical formula 18]

[0129]

[0130] 4.0 g (7.26 mmol) of the L-rhamnose bis(dodecyl)thioacetal (XVI) obtained in Example 1 above was dissolved by heating in 100 mL of acetic acid. To this solution, 40 mL of 30% aqueous hydrogen peroxide was added little by little under vigorous stirring, and after the addition was complete, stirring was continued at room temperature for 18 hours. The reaction solution from which a white precipitate precipitated was diluted with water, extracted with ethyl acetate, and the extract was dried and concentrated. Filter the resulting white precipitate, and obtain 4.02 g (yield 90%) of 1,1-bis(dodecylsulfonyl)-1-mannose-2,3,4,5-tetrahydrohexane (XVII) by drying . This product can be directly carried out in the next process, and colorless needle crystals can be obtained by recrystallization in acetic acid.

[0131] Melting point: 11...

Embodiment 3

[0134] Example 3: Production of 5-deoxy-L-arabinose (VIII)

[0135] [chemical formula 19]

[0136]

[0137] Dissolve 1.00 g (1.62 mmol) of 1,1-bis(dodecylsulfonyl)-1-mannose-2,3,4,5-tetrahydrohexane obtained in Example 2 above in 10 mL of dioxane (XVII), add 5 mL of 28% ammonia water under stirring. The mixture was stirred at room temperature for 1 hour, the precipitated white crystalline precipitate bis(dodecylsulfonyl)methane was removed by filtration, and the filtrate was concentrated. Water was added to the residue, extracted twice with chloroform, and the combined organic solvent was distilled off to obtain 0.17 g (yield 80%) of 5-deoxy-L-arabinose (VIII) as a pale yellow oil.

[0138] IR spectrum (cm -1 ): 3350, 1650, 1560, 1450, 1410, 1380, 1310, 1125, 1060, 1030, 980, 835.

[0139] NMR spectrum (D 2 O / ppm): 5.10 (1H, d), 5.07 (1H, d), 3.99 (1H, m), 3.90 (1H, m), 3.58 (1H, m), 1.63 (3H, d).

[0140] Each of the above-mentioned Examples 1 to 3 did not generate t...

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Abstract

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.

Description

technical field [0001] The present invention relates to a method for producing a compound in which the carbon atoms of aldoses are reduced by one, and in particular to (R)-2-amino-6-[(1R, 2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(3H)-pteridone (dihydrochloride is the common name: sapropterin hydrochloride (sapropterin hydrochloride) An industrially excellent new production method of 5-deoxy-L-arabinose useful as a synthetic intermediate of ). Background technique [0002] [chemical formula 1] [0003] [0004] The indicated L-erythro-biopterin is one of the pteridines widely present in nature, and is a compound present in microorganisms, insects, algae, amphibians, and mammals (Non-Patent Document 1). The following formula (B) as its tetrahydro body: [0005] [chemical formula 2] [0006] [0007] Represented (R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(3H)-pteridinone (hereinafter Sometimes it is also abbreviated as R-THBP) because of its ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/02C07H3/08C07C317/18C07C323/12
CPCC07H3/08C07C319/14C07C315/02C07H3/02C07C317/18C07C323/12
Inventor 兴津光人龟位胜秀
Owner ASUBIO PHARMA
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