83465-22-9

Basic information

• Product Name: Valiolamine
• Synonyms: 5-AMINO-1-(HYDROXYMETHYL)CYCLOHEXANE-1,2,3,4-TETRAOL;VALIOLAMINE;4-amino-3,4-dideoxy-2-c-(hydroxymethyl)-d-epi-inositohydrate;4-amino-3,4-dideoxy-2-c-(hydroxymethyl)-d-epi-inositolhydrate;VALIOLAMINE (4-AMINO-3,4-DIDEOXY-2-C-(HYDROXYMETHYL)-D-EPI-INOSITO);(1S,2S,3R,4S,5S)-5-Amino-1-hydroxymethylcyclohexane-1,2,3,4-tetranol;(1S)-1,2β,3α,4β-Tetrahydroxy-5β-aminocyclohexane-1α-methanol;4-Amino-3,4-dideoxy-2-C-(hydroxymethyl)-D-epi-inositol
• CAS NO: 83465-22-9
• Molecular Formula: C₇H₁₅NO₅
• Molecular Weight: 193.2
• Product Categories: Miscellaneous Biochemicals;VOGLIBOSE
• Mol File: 83465-22-9.mol

Chemical Properties

• Boiling Point: 368.6 °C at 760 mmHg
• Flash Point: 176.7 °C
• Appearance: /
• Density: 1.623 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Sparingly)
• PKA: 13.27±0.70(Predicted)
• CAS DataBase Reference: Valiolamine(CAS DataBase Reference)
• NIST Chemistry Reference: Valiolamine(83465-22-9)
• EPA Substance Registry System: Valiolamine(83465-22-9)

Safety Data

• Hazardous Substances Data: 83465-22-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Valiolamine is used as a pharmaceutical agent for its alpha-D-glucosidase inhibitory activity. Its ability to inhibit the activity of porcine intestinal sucrase, maltase, and isomaltase makes it a potential candidate for the development of drugs to treat diabetes and other related conditions.
Used in Healthcare Industry:
Valiolamine is used in healthcare applications to manage and control blood sugar levels. Its alpha-D-glucosidase inhibitory activity helps in slowing down the digestion of carbohydrates, thereby reducing the rate of glucose absorption in the bloodstream. This can be beneficial for individuals with diabetes or those at risk of developing the condition.

InChI:InChI=1/C7H15NO5/c8-3-1-7(13,2-9)6(12)5(11)4(3)10/h3-6,9-13H,1-2,8H2/t3-,4-,5+,6-,7-/m0/s1

Upstream product

• 85281-06-7 <1S-(endo,exo,endo)>-6,7,8-trihydroxy-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo<3.3.1>nonane 
• 85240-34-2 1-(bromomethyl)-6,7,8-trihydroxy-3-oxo-2-oxa-4-azabicyclo<3.3.1>nonane 
• 85240-32-0 6,7,8-triacetoxy-1-(bromomethyl)-3-oxo-2-oxa-4-azabicyclo<3.3.1>nonane 
• 183505-14-8 (1S,2S,3R,4S,5S)-1-azido-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol 
• 1054620-36-8 N-((1S,2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-2,5-dihydroxy-cyclohexyl)-4-methyl-benzenesulfonamide 
• 693245-47-5 (1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7-ol 
• 694527-29-2 1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4,5-tetra-O-acetyl-1,2,3,4,5-cyclohexanepentol 
• 220939-94-6 (3S,4R)-1,3,4-tris(benzyloxy)-hex-5-en-2-one 
• 135735-90-9 (1R,2R,3S)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohex-4-en-1,2,3-triol 
• 171252-89-4 (1R,2S,3R,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-O-(trifluoromethanesulfonyl)cyclohexane-1,2,3,4,5-pentol 
• 183268-64-6 (1S,2R,3S,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-2-O-(trifluoromethanesulfonyl)cyclohexane-2,3,4,5-tetrol 
• 171252-88-3 (1R,2R,3R,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-1,2,3,4,5-pentol 
• 171252-90-7 (1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol 
• 171339-44-9 (1R,2S,3S,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O,O-sulfonylcyclohexane-1,2,3,4,5-pentol 

Downstream Products

• 83470-45-5 N-(3-pyridylmethyl)valiolamine 
• 83470-43-3 N-thenylvaliolamine 
• 101540-72-1 N-<(S)-α-(hydroxymethyl)benzyl>valiolamine 
• 101540-71-0 N-<(R)-α-(hydroxymethyl)benzyl>valiolamine 
• 83480-29-9 voglibose 
• 83541-27-9 N-<(S)-β-hydroxyphenethyl>valiolamine 
• 83470-49-9 N-cyclohexylvaliolamine 
• 89859-79-0 methyl 4-<<(1S,2S)-(2,4,5(OH)/3,5)-2,3,4,5-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>amino>-4,6-dideoxy-α-D-glucopyranoside 
• 90024-25-2 methyl 4-<<(1S,2S)-(2,4,5(OH)/3,5)-2,3,4,5-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>amino>-4,6-dideoxy-α-D-galactopyranoside 
• 89859-81-4 methyl 4-<<(1S,2S)-(2,4,5(OH)/3,5)-2,3,4,5-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>amino>-4-deoxy-α-D-glucopyranoside 
• 90024-26-3 methyl 4-<<(1S,2S)-(2,4,5(OH)/3,5)-2,3,4,5-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>amino>-4-deoxy-α-D-galactopyranoside 
• 89860-05-9 N-<(1R,2S)-(2,6/3,4)-4-amino-2,3-dihydroxy-6-methylcyclohexyl>valiolamine 
• 89920-31-0 N-<(1S,2S)-(2,6/3,4)-4-amino-2,3-dihydroxy-6-methylcyclohexyl>valiolamine 
• 83470-38-6 N-(4-bromobenzyl)valiolamine 

Relevant articles and documents

Synthesis method of valiolamine key intermediate

The invention relates to a synthesis method of a valiolamine key intermediate IV. According to the method, valiolamine is used as a raw material to prepare the key intermediate IV through amino protection, 4-site dydroxymethyl iodideo reaction, 1,2,3-site three-hydroxyl protection, hydrogen iodide removal and double-bond forming; the key intermediate IV can be used for synthesizing valiolamine.

Method for preparing voglibose and corresponding intermediate

The invention relates to a novel intermediate for preparing voglibose and a preparation method of the voglibose. In particular, the intermediate is shown as a formula II as shown in the specification.The intermediate is prepared by a reaction of a compound shown as a formula I with peroxide; in addition, the intermediate can be hydrolyzed to form valiolamine; and voglibose is further synthesized.The method is simple, environmentally-friendly and high in yield.

Volt-voglibose intermediate and its preparation method

The invention relates to a voglibose intermediate as shown in the following formula V and a preparation method of the voglibose intermediate and also relates to a preparation method of a voglibose intermediate 1L(1S)-(1(OH), 2, 4, 5/1, 3)-5-amino-1-C-(hydroxymethyl)-1, 2, 3, 4-tetrahydroxycyclohexane. The method comprises the steps: with a validamycin fermentation byproduct 1L(1, 3, 4/2)-4-amino-6-hydroxymethyl-1, 2, 3-trihydroxycyclohexane as a raw material, carrying out amino protection, elimination, epoxidation, hydrolysis and deprotection reaction to obtain valiolamine. Compared with the traditional synthesis method, the method disclosed by the invention is few in synthesis step, little in pollution due to the adoption of a recyclable efficient catalyst, simple in operation and stable in yield.

Amino sugar compound and preparation method and application thereof

The invention discloses an amino sugar compound as shown in formula I, a preparation method of the amino sugar compound and application of the amino sugar compound to the preparation of a compound as shown in formula A.

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.

Total syntheses of (+)-valiolamine and (-)-1-epi-valiolamine from naturally abundant (-)-shikimic acid

Total syntheses of (+)-valiolamine (1) and (-)-1-epi-valiolamine (2) from the naturally abundant (-)-shikimic acid are described. Ethyl 3-epi-5-O-methylsulfonyl-shikimate (3), as the key common intermediate, was first synthesized in five steps in 74 % overall yield, and then converted into the targets 1 and 2 in seven steps in 48 and 41 % overall yield, respectively. Copyright

Diastereospecific epoxidation and highly regioselective ring-opening of (+)-valienamine: Practical synthesis of (+)-valiolamine

An efficient and practical synthesis of (+)-valiolamine starting from readily available aminocyclitol (+)-valienamine in five steps and up to 80% total yield in gram-scale quantities is reported. Diastereospecific epoxidation by means of substrate directable reaction and regioselective ring-opening of corresponding epoxide are the key reactions in the synthesis, which circumvent laborious purification of products using chromatographical separation. The detailed mechanisms of epoxidation and ring-opening attacked by halide, including the directing and steric hindrance effect, are also discussed.

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

Intramolecular direct Aldol reactions of sugar diketones: Syntheses of valiolamine and validoxylamine G

(Chemical Equation Presented) A new and stereoselective intramolecular direct aldol reaction of diketones derived from carbohydrates has been developed to construct carbocycles with D-gluco-, D-galacto, D-manno-, and L-ido-configurations. The stereochemical outcome of the aldol reaction of the diketone is dependent on the base used. Transformation of D-gluco-aldols readily affords valiolamine which also constitutes a formal synthesis of voglibose. Facile conversion of D-gluco-cyclohexanones into validoxylamine G has been achieved in 12 steps with 15.1% overall yield from D-glucose.

PROCESS FOR THE PREPARATION OF 1,2,3,4-CYCLOHEXANETETROL DERIVATIVES

Provided herein are processes for the preparation of 1,2,3,4-cyclohexanetetrol derivatives, which are useful intermediates for the synthesis of voglibose; processes for the preparation of substituted 2,3,4,5-tetrahydroxycyclohexanone; and processes for preparing voglibose. Also provided are compounds formed by such processes.