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
• Article Data: 16

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

Description

Valiolamine is an aminocyclitol, a type of sugar alcohol, that is known for its potent alpha-D-glucosidase inhibitory activity. It effectively inhibits the activity of porcine intestinal sucrase, maltase, and isomaltase, making it a promising candidate for various applications in the pharmaceutical and healthcare industries.

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

• 1476028-69-9 (3R,4R,5R)-ethyl 3,4-epoxy-5-(methylsulfonyloxy)cyclohex-1-ene-1-carboxylate 
• 1476028-68-8 (3R,4S,5R)-ethyl 3,4-epoxy-5-hydroxycyclohex-1-ene-1-carboxylate 
• 1054636-37-1 (1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane 
• 148347-73-3 (1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate 
• 1476028-67-7 (3S,4S,5R)-ethyl 3-chloro-4,5-bis(formyloxy)cyclohex-1-ene-1-carboxylate 
• 1476028-77-9 (1S,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate 
• 1476028-75-7 (3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 1476028-73-5 (3S,4S,5S)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate 
• 1476028-71-3 (3S,4S,5S)-ethyl 5-azido-3,4-dihydroxycyclohex-1-ene-1-carboxylate 
• 1476028-70-2 (3S,4R,5R)-5-methanesulfonyloxy-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester 
• 1377616-68-6 C₁₈H₂₁NO₆ 

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 
• 1303996-67-9 C₁₇H₃₄N₂O₁₁ 
• 1303996-67-9 C₁₇H₃₄N₂O₁₁ 

Relevant articles and documents

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.

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.