112653-29-9

Basic information

• Product Name: AO 128
• Synonyms: 2,3-Dideoxy-2-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-4-C-(hydroxymethyl)-epi-inositol; 5-(2-Hydroxy-1-(hydroxymethyl)ethyl)amino-1-C-(hydroxymethyl)-1,2,3,4-cyclohexanetetrol; BRN 5430708; CCRIS 4540; Epi-inositol, 2,3-dideoxy-2-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-4-C-(hydroxymethyl)-; 5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol; (1S,2S,3R,4S,5S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
• CAS NO: 112653-29-9
• Molecular Formula: C10H21NO7
• Molecular Weight: 267.276
• Mol File: 112653-29-9.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 601.9°C at 760 mmHg
• Flash Point: 274.1°C
• Appearance: /
• Density: 1.58g/cm³
• Vapor Pressure: 5.37E-17mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: AO 128(CAS DataBase Reference)
• NIST Chemistry Reference: AO 128(112653-29-9)
• EPA Substance Registry System: AO 128(112653-29-9)

Safety Data

• Hazardous Substances Data: 112653-29-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H21NO7/c12-2-5(3-13)11-6-1-10(18,4-14)9(17)8(16)7(6)15/h5-9,11-18H,1-4H2/t6-,7-,8+,9-,10-/m0/s1

Upstream product

• 115250-39-0 (1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol 
• 116308-18-0 (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-dichloro-5-oxo-1,2,3,4-cyclohexanetetrol 
• 140658-50-0 (2R,3R,4S,5R,6R)-3,4,5-tris-benzyl-6-benzyloxymethyl-2-dichloromethyltetrahydro-2H-pyran-2-ol 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 82920-27-2 N-<2-hydroxy-1-(hydroxymethyl)ethyl>valienamine 
• 38231-86-6 valienamine 
• 849419-34-7 voglibose hydrochloride 
• 115250-38-9 (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol 
• 96-26-4 dihydroxyacetone 

Relevant articles and documents

Structural identification of 4-benzyl-voglibose hydrochloride monohydrate using NMR and single-crystal X-ray diffraction methods

The chemical structure studies on an important related substance of voglibose have been carried out using NMR spectroscopy and single crystal X-ray crystallography. For the structure identification study, hydrochloride monohydrate of this compound was iso

Preparation method of voglibose

The invention discloses a preparation method of voglibose. The preparation method comprises the steps of adopting tetrabenzyl voltolose as a raw material for a reaction in an aprotic solvent in the presence of boron halide, and adding a basic substance for crystallization, suction filtration and recrystallization to obtain the high-purity and high-yield voglibose after the reaction is completed. The whole synthesis process has the advantages that the raw material cost is extremely low, the reaction time is short, and the product yield and the quality are high; the method is suitable for industrial production.

Preparation method for voglibose

The invention discloses a preparation method for a drug namely voglibose (AO128) I for treatment of diabetes. With the preparation method provided by the invention, a target product with a yield of atleast 15% is obtained through seven steps by using an intermediate II derived from shikimic acid as a raw material. The method comprises the following steps: with a ring-opening product II as a starting raw material, allowing the ring-opening product II to undergo nucleophilic substitution with sodium azide so as to obtain a configuration-inverted intermediate III; allowing the intermediate III to react with benzoyl chloride so as to obtain a product IV; then allowing double bonds of the product IV to undergo high-selectivity catalytic oxidation through rhodium so as to obtain a diol productV; reducing an ester group of the diol product V through sodium borohydride so as to obtain a compound VI containing three hydroxyl groups; protecting the primary hydroxyl group and the secondary hydroxyl group of the compound VI so as to obtain an intermediate VII; allowing the intermediate VII to connect with dibenzoyl oxyacetone for further reduction so as to obtain a compound VIII; and removing all protecting groups from the compound VIII by one step so as to obtain a target product I, i.e., the voglibose (AO128). The preparation method provided by the invention has the advantages of cheapand easily-available raw materials and used reagents, high stereoselectivity, high yield and possibility of industrial production.