112653-29-9

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

• 96-26-4 dihydroxyacetone 
• 83465-22-9 (1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane 
• 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 
• 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 
• 849419-34-7 voglibose hydrochloride 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 140658-50-0 (2R,3R,4S,5R,6R)-3,4,5-tris-benzyl-6-benzyloxymethyl-2-dichloromethyltetrahydro-2H-pyran-2-ol 
• 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 
• 82920-27-2 N-<2-hydroxy-1-(hydroxymethyl)ethyl>valienamine 

Relevant academic research and scientific papers

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

Synthesis method of voglibose

The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.

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.

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.

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.

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.

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.

HYPOGLYCEMIC EFFECT ENHANCER

A hypoglycemic effect enhancer for enhancing the activity of an α-glucosidase inhibitor, the enhancer comprising at least one kind of bacteria selected from the group consisting of bifidobacteria, lactic acid bacteria, saccharifying bacteria, and butyric acid bacteria.

PROCESSES FOR THE PURIFICATION OF VOGLIBOSE AND INTERMEDIATES THEREOF

Processes for the purification of voglibose are provided. Also provided are processes for the purification of substituted or unsubstituted 5-oxo-1,2,3,4-cyclohexanetetrol and substituted 5-amino-1,2,3,4-cyclohexanetetrol, which compounds are useful intermediates in the preparation of voglibose.

USE OF SUBSTITUTED 2 PHENYLBENZIMIDAZOLES AS MEDICAMENTS

The present invention relates to the use of a substituted 2-phenylbenzimidazole of formula I wherein R1, R2, R3, R 4, R5 and m have the meanings given in the claims, for the preparation of a medicament for the treatment or prevention of diseases involving glucagon receptors, as well as new compounds of formula I wherein R1 is a group of formula