38231-86-6

Usage

Uses

Used in Pharmaceutical Industry:
Valienamine is used as a glucosidase inhibitor for its ability to inhibit the activity of glucosidase enzymes without undergoing hydrolysis. This property makes it a potential candidate for the development of drugs targeting conditions related to glucose metabolism.
Used in Chemical Research:
As a slightly yellow solid with distinctive chemical properties, Valienamine is also used in chemical research for studying enzyme inhibition mechanisms and the development of novel compounds with similar or improved properties for various applications.
Used in Drug Development:
Valienamine's unique ability to inhibit glucosidase enzymes without undergoing hydrolysis makes it a valuable compound in the development of new drugs for treating diseases related to glucose metabolism, such as diabetes and certain genetic disorders.

InChI:InChI=1/C7H13NO4/c8-4-1-3(2-9)5(10)7(12)6(4)11/h1,4-7,9-12H,2,8H2

Upstream product

• 119951-76-7 Benzoic acid (1R,2S,3R,4S,5R,6R)-2,4,5-triacetoxy-3-benzyloxy-1-hydroxy-6-nitro-cyclohexylmethyl ester 
• 38665-10-0 (+)-validoxylamine A 
• 148291-19-4 bis[(1S,2S,3S,4R)-2,3,4-trihydroxy-5-(hydroxymethyl)-5-cyclohexenyl]amine 
• 202339-50-2 6-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid ethyl ester 
• 221371-27-3 (1R,2S,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O,O-sulfonylcyclohex-5-ene-1,2,3,4-tetraol 
• 183268-55-5 (1R,2R,3S,4S,5S)-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 
• 227930-72-5 (1D)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-C-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3,4-tetrol 
• 110205-68-0 1,3,4,5-tetra-O-benzyl-6,7-dideoxy-L-xylo-hept-6-en-2-ulose 
• 85240-37-5 N-(tert-butyloxycarbonyl)-valienamide 
• 913069-83-7 Succinic acid mono-((3S,4S,5S,6R)-3-tert-butoxycarbonylamino-4,5,6-trihydroxy-cyclohex-1-enylmethyl) ester 
• 2280-44-6 D-Glucose 
• 227930-76-9 (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol 
• 37248-47-8 validamycin A 
• 107960-21-4 Benzoic acid (3S,4S,5S,6R)-4,5,6-tris-benzyloxy-3-(toluene-4-sulfonylamino)-cyclohex-1-enylmethyl ester 

Downstream Products

• 85240-37-5 N-(tert-butyloxycarbonyl)-valienamide 
• 83470-76-2 N-(benzyloxycarbonyl)valienamine 
• 1137669-84-1 C₁₇H₂₃NO₉ 
• 38231-88-8 (+)-valienamine hydrochloride 
• 89859-74-5 methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4-deoxy-α-D-glucopyranoside 
• 89920-25-2 methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4-deoxy-α-D-galactopyranoside 
• 80943-41-5 methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4,6-dideoxy-α-D-glucopyranoside 
• 89920-24-1 methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4,6-dideoxy-α-D-galactopyranoside 
• 74645-52-6 (1L)-(1,3,4/2)-4-acetamido-1,2,3-tri-O-acetyl-4-[(acetoxy)methyl]cyclohex-5-ene-1,2,3-triol 
• 82920-27-2 N-<2-hydroxy-1-(hydroxymethyl)ethyl>valienamine 
• 134241-83-1 valienamine 7-α-isomaltoside 
• 134221-44-6 valienamine 4-α-isomaltoside 
• 134221-43-5 valienamine 4-α-glucoside 
• 134221-45-7 valienamine 7-α-glucoside 

Relevant academic research and scientific papers

A new pre-column derivatization for valienamine and beta-valienamine using o-phthalaldehyde to determine the epimeric purity by HPLC and application of this method to monitor enzymatic catalyzed synthesis of beta-valienamine

Valienamine and β-valienamine are representative C7?N aminocyclitols with significant glycosidase inhibition activity that have been developed as important precursors of drugs for diabetes and lysosomal storage diseases, respectively. The quantitative analysis of these chiral compounds is crucial for asymmetric in vitro biosynthetic processes for converting valienone into valienamine epimers using aminotransferase. Here, we developed an efficient and sensitive method for separation and quantitative analysis of chiral valienamine using reversed-phase high-performance liquid chromatography (HPLC) through o-phthalaldehyde (OPA) pre-column derivatization of the analytes. The epimers were derivatized by OPA in borate buffer (pH 9.0) at room temperature for 30 s, separated on an Eclipse XDB-C18 (5?μm, 4.6?×?150?mm) column, eluted with 22% acetonitrile at 30?°C for 18?min, and detected by a fluorescence detector using 445?nm emission and 340?nm excitation wavelengths. The average resolution of the epimers is 3.86, and the concentration linearity is in the range of 0.02–20?μg/ml. The method proved to be effective, sensitive, and reliable with good intra- and inter-day precision and accuracy, and successfully evaluated the enantiopreference and catalytic capability of the potential aminotransferases on an unnatural prochiral substrate, facilitating the design of an asymmetric biosynthetic route for optically pure valienamine and β-valienamine.

Improved Stereoselective Syntheses of (+)-Valiolamine and (+)-Valienamine Starting from (–)-Shikimic Acid

Improved stereoselective syntheses of the target compounds (+)-valiolamine 1 and (+)-valienamine 2 starting from naturally abundant (–)-shikimic acid are described. A common key intermediate compound 7 was first synthesized from (–)-shikimic acid in 9 steps. The compound 7 was then converted to (+)-valiolamine 1 in 3 steps, and was also converted to (+)-valienamine 2 in 4 steps. In summary, (+)-valiolamine 1 and (+)-valienamine 2 were synthesized from (–)-shikimic acid in 12 (or 13) steps in 40% and 39% overall yields, respectively. The present syntheses are more practical and might be important for the potential industrial preparations of pharmaceutically valuable (+)-valiolamine 1 and (+)-valienamine 2.

Stereoselective synthesis of (+)-valienamine starting from the naturally abundant (-)-shikimic acid

A stereoselective synthesis of the pharmaceutically useful pseudo-aminosugar (+)-valienamine 1 is described. Epoxide 2 was first prepared via four steps in 79.7% overall yield starting from the naturally abundant (-)-shikimic acid. Epoxide 2 was then converted into the vicinal dihydroxyl compound 3 in 96% yield via a highly regio- and stereoselective water-mediated epoxide opening. Compound 3 was transformed into compound 4 in 86% yield over two steps via ester-reduction and benzylation of the three hydroxyl groups. Compound 4 was converted into azido compound 5 in 90% yield via an SN2-type nucleophilic substitution of the OMs leaving group with sodium azide. Ruthenium-catalyzed stereoselective dihydroxylation of compound 5 afforded dihydroxyl compound 6 in 91% yield. Compound 6 was transformed into compound 7 in 92% yield via selective mono-acetylation of the less-hindered hydroxyl group. Dehydration of tertiary alcohol 7 via an acid-mediated elimination furnished olefinic compound 8 in 85% yield. Finally, compound 8 was converted into the title compound 1 in 91% yield over two steps via deprotection and Lindlar-catalyst-promoted highly selective hydrogenation of the azido group (N3) in the presence of a double bond. (+)-Valienamine 1 was thus synthesized starting from the naturally abundant (-)-shikimic acid via 13 steps in 38.3% total yield.

Novel synthesis method of violienamine

The invention provides a novel synthesis method of violienamine. Specifically, the invention provides the novel synthesis method comprising the following steps: carrying out double-bond epoxidation reaction on an intermediate I to obtain an intermediate II; then carrying out rearrangement reaction on the intermediate I to obtain an intermediate III, i.e., violienamine with an amino protection group; removing the protection group from the intermediate II to obtain violienamine.

Preparation method of high-purity validamine

Validamine and valienamine are important chemical raw materials but have high separation cost and complex separation process. The invention discloses a preparation method validamine, which includes the steps of: 1) hydrolyzing validoxylamine A through an NBS chemical method by adding the validoxylamine A and NBS to water as a solvent according to certain molar ratio, and performing a reaction for 4 h at 25 DEG C; 2) carrying out adsorption separation to the reaction product through a weak-acidic cation exchange resin, and concentrating the product to obtain a mixture of the validamine and valienamine; 3) under catalysis by a heavy metal catalyst, performing hydrogenation to the mixture, performing adsorption separation to the reaction product through a weak-acidic cation exchange resin, concentrating the product, and vacuum-drying the concentrate to obtain a high-quality validamine sample.

Amino sugar intermediate preparation method

The present invention discloses a method for preparing a compound amino sugar intermediate represented by a formula I through a one-step method, a composition containing the compound represented by the formula I and a compound represented by a formula A and obtained through the method, and uses of the composition in preparation of type 2 diabetes treating drugs. The formulas I and A are defined in the specification.

Total synthesis of (+)-valienamine and (-)-1-epi-valienamine via a highly diastereoselective allylic amination of cyclic polybenzyl ether using chlorosulfonyl isocyanate

The total synthesis of (+)-valienamine and (-)-1-epi-valienamine was concisely accomplished from readily available d-glucose via a highly diastereoselective amination of chiral benzylic ether using chlorosulfonyl isocyanate, intramolecular olefin metathesis, and diastereoselective reduction of cyclic enone using l-Selectride as the key steps.

Methods of producing validamycin A analogs and uses thereof

This disclosure relates to validamycin A biosynthesis and in particular, to methods of producing validamycin A analogs and uses thereof. In a particular example, a method for making a validamycin A analog includes transforming a host cell with one or more recombinant DNA vectors to produce a valN-inactivated mutant; and culturing the valN-inactivated mutant in a culture medium to produce a validamycin A analog, such as 1,1′-bis-valienamine and validienamycin, and their conversion to valienamine. The present disclosure further relates to compositions including such compounds as well as methods of using the compositions, such as for antifungal agents.

A C2-symmetric pool based flexible strategy: An enantioconvergent synthesis of (+)-valiolamine and (+)-valienamine

A new enantioconvergent strategy directed toward the synthesis of glucosidase inhibitors was developed by using a C2-symmetric element within the chiral pool and by applying an iodine-promoted cyclization of an unsaturated carbonimidothioate for the regio- and diastereocontrolled installation of amino and hydroxy units. Not only does this simple flexible strategy provide a convergent concise approach to (+)-valiolamine (1), but it can also be readily adopted for the synthesis of (+)-valienamine (2). Commercially available and cheap C2-symmetric D-tartaric acid served as the chiral building block. Copyright

A concise synthetic approach to (+)-valienamine starting from Garner's aldehyde

A synthesis of (+)-valienamine was achieved starting from Garner's aldehyde in ten steps and 23% overall yield. A unique feature of the synthetic route is that an acyclic precursor was constructed, using diastereoselective antireductive coupling reaction of alkyne and Garner's aldehyde as the key step, which was then cyclized in an intramolecular aldol reaction to form the valienamine skeleton. Georg Thieme Verlag Stuttgart · New York.