13039-56-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Deoxy-L-arabinose is used as a key intermediate in the synthesis of various pharmaceutical compounds, including antibiotics, antivirals, and anticancer drugs. Its unique structure allows for the development of novel drugs with improved efficacy and reduced side effects.
Used in Food Industry:
5-Deoxy-L-arabinose is used as a natural sweetener and bulking agent in the food industry. Its low glycemic index makes it a suitable alternative for people with diabetes or those looking to reduce their sugar intake.
Used in Cosmetic Industry:
5-Deoxy-L-arabinose is used as a humectant and moisturizing agent in cosmetic products. Its ability to retain moisture helps to keep the skin hydrated and maintain its elasticity.
Used in Enzyme Inhibition:
5-Deoxy-L-arabinose shows a strong inhibitory effect on β-galactosidase of Escherichia coli. This property can be utilized in various applications, such as the development of new antibiotics or the study of enzyme mechanisms.

InChI:InChI=1/C5H10O4/c1-2-3(6)4(7)5(8)9-2/h2-8H,1H3/t2-,3?,4+,5?/m0/s1

Upstream product

• 13039-80-0 5-deoxy-L-(+)-arabinose-diethylmercaptal 
• 93978-94-0 5-deoxy-β-L-arabinose 
• 132130-06-4 L-arabino-3,4,5-triacetoxy-1,1-bis-ethanesulfonyl-hex-1-ene 
• 5328-37-0 L-arabinose 
• 43179-48-2 L-arabinose di(ethylthio)acetal 
• 1352707-53-9 1',3'-propanedisulfonyl (L)-rhamnose 
• 3615-41-6 L-Rhamnose 
• 24807-89-4 2,3,4,5-tetra-O-acetyl-L-rhamnose diethyl dithioacetal 
• 6748-70-5 L-rhamnose diethyl dithioacetal 
• 13039-79-7 5-tosyl-L-(+)-arabinose-diethylmercaptal 
• 488-28-8 L-rhamnitol 
• 7732-18-5 water 
• 93978-95-1 5-deoxy-α-L-arabinose 
• 54253-49-5 1,1-diethylsulfonyl-L-rhamnose 

Downstream Products

• 22150-76-1 biopterin 
• 76647-70-6 (3R,4R,5S)-3,4-dihydroxy-5-methyldihydrofuran-2(3H)-one 
• 13039-60-6 L-erythro-5-deoxy-[2]pentosulose-bis-phenylhydrazone 
• 5531-26-0 L-erythro-5-deoxy-[2]pentosulose-bis-(4-bromo-phenylhydrazone) 
• 93978-94-0 5-deoxy-β-L-arabinose 
• 93978-95-1 5-deoxy-α-L-arabinose 
• 2636-52-4 L-Primapterin 
• 94591-31-8 2-N-Benzoyl-1',2'-di-O-benzoyl-4-thiobiopterin 
• 94591-29-4 2-N-Benzoyl-1',2'-di-O-benzoylbiopterin 
• 94591-24-9 Biolumazin 
• 62933-57-7 1',2'-O-diacetyl-L-biopterin 
• 95895-36-6 5-deoxy-2,3,4-O-triacetyl-L-arabinose-phenylhydrazone 
• 59245-36-2 (2S,3S,4S)-1-(Phenyl-hydrazono)-pentane-2,3,4-triol 
• 59245-36-2 5-deoxy-L-arabinose phenylhydrazone 

Relevant academic research and scientific papers

Pterin chemistry: A simple synthesis of 5-deoxy-L-[5-2H1]arabinose and L-[3'-2H1]biopterin

A simple synthesis of 5-deoxy-L-[5-2H1]arabinose was performed to obtain L-[3'-2H1]biopterin. The reduced form of this model substance is needed to investigate the pathway of 7-substituted pterins in patients with primapterinuria.

5-deoxy-L-arabinose synthesis method

The invention provides a synthesis method for preparing 5-deoxy-L-arabinose through a three-step two-pot method. According to the synthesis method, a natural product L-rhamnose is used as a starting material, a condensation and oxidation one-pot reaction is performed to obtain a high-purity oxidation intermediate, and an aminolysis reaction is performed to obtain the high purity 5-deoxy-L-arabinose aqueous solution. According to the present invention, the preparation method has the simple operation, can avoid the disadvantages of strong acid, bad smell and the like, is suitable for industrial production, can obtain the high-purity oxidation intermediate, and is suitable for the control of the starting material related substance in the drug synthesis process.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF METABOLIC DISEASES

The invention relates to the compounds of formula I, formula II and formula III or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, formula II or formula III; and methods for treating or preventing metabolic diseases may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of phenylketonuria, cardiovascular disease, autism, ADHD, hypertension, endothelial dysfunction and chronic kidney disease.

PROCESS FOR THE PREPARATION OF PTERIDINE DERIVATIVES

The application discloses a process for the preparation of 5-deoxy-L-arabinose of formula (VI); comprising the conversion of a compound of formula (XII); wherein n is 0, 1 or 2; which can be used as intermediate for the synthesis of sapropterin.

PROCESS FOR THE PREPARATION OF PTERIDINE DERIVATIVES

The application discloses a process for the preparation of 5-deoxy-L-arabinose of formula (VI); comprising the conversion of a compound of formula (XII); wherein n is 0, 1 or 2; which can be used as intermediate for the synthesis of sapropterin.

Crystalline polymorph of biopterin and production method thereof

Crystalline solids A to E of biopterin are distinguished from each other by diffraction angle in an X-ray powder diffraction pattern measured using Cu—Kα radiation. The crystalline solid A is characterized by strong peak at 4.6° and peaks at 13.6°, 18.1° and 27.5°; the crystalline solid B is characterized by strong peak at 4.85° and peaks at 2.4°, 13.2°, 18.1° and 27.3°; the crystalline solid C is characterized by strong peak at 5.35° and peaks at 10.8°, 21.9° and 27.3°; the crystalline solid D is characterized by strong peak at 5.1° and peaks at 2.6°, 9.2°, 13.4°, 15.4°, 18.3°, 21.8° and 27.3°; and the crystalline solid E is characterized by strong peaks at 4.5° and 5.8°, and peaks at 10.6°, 15.6°, 20.0°, 20.7°, 23.8° and 27.3°.

PROCESS FOR PRODUCING CARBON-DIMINISHED ALDOSE COMPOUND

The present invention provides a process capable of industrially producing 5-deoxy-L-arabinose, important as a raw material for the production of sapropterin useful as a therapeutic agent for atypical hyperphenylalaninemia, satisfactorily efficiently even with a simple production apparatus. Provided is the process for producing 5-deoxy-L-arabinose characterized by including: reacting L-rhamnose with a C11-16 straight chain alkyl mercaptan compound in the presence of an acid catalyst to prepare L-rhamnose dialkylmercaptal; subjecting then the obtained compound to an oxidation reaction to prepare a sulfonyl derivative; and subjecting then the sulfonyl derivative to a carbon-reduction reaction to prepare 5-deoxy-L-arabinose. The present production process can also be applied to a process for producing compounds obtained by removing one carbon atom from other aldol compounds, and thus the present invention provides a general process for producing compounds obtained by reducing the number of carbon atoms from aldose compounds.

Method for producing L-biopterin

To provide a method for producing L-biopterin on a large industrial scale by using a reagent which is inexpensive and easy to handle, without requiring a use of any particular equipment or plants.

Intermediates for preparing optically active carboxylic acids

A process is described for preparing optically active alpha-arylalkanoic acids consisting of rearranging an optically active ketal of formula STR1 in which the substituents have the meaning given in the description of the invention.

FURANOSE RING ANOMERIZATION: A KINETIC STUDY OF THE 5-DEOXYPENTOSES AND 5-O-METHYLPENTOSES

The anomerzation of 5-deoxy-L-pentoses (1-4) and 5-O-methyl-D-pentoses (5-8) in aqueous solution has been studied by (13)C saturation-transfer n.m.r. (s.t.-n.m.r.) spectroscopy, using compounds substituted with (13)C at the anomeric carbon atom.Unidirectional rate-constants of ring-opening (kopen) and ring closing (kclose) have been obtained for these compounds under identical solution conditions (50mM acetate buffer, pH 4.0 at 60 deg C), and have been compared to those measured for the D-tetroses (9 and 10) and four D-pentose 5-phosphates (11-14).Based on these comparisons, several correlations between furanose structure and reactivity have been revealed, and models have been proposed to explain the observed kinetic behavior of compounds 1-10.The effect of exocyclic structure on acid-catalyzed rate-constants was also examined by comparing the behavior of 5-deoxy-L-lyxose and 5-O-methyl-D-lyxose.Some consideration has been given to identifying the factors (enthalpic and entropic) that may play roles in determining the effect of structure on anomerization reactivity.