Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

D-fructopyranose derived saccharide beta-alkamine and synthesis method thereof

A synthesis method and technology of amino alcohols, applied in sugar derivatives, sugar derivatives, preparation of sugar derivatives, etc., to achieve the effects of cheap and easy-to-obtain raw materials, mild reaction conditions, and easy operation

Inactive Publication Date: 2011-09-14
NANJING UNIV OF SCI & TECH
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Existing the synthetic method of many carbohydrate β-aminoalcohols is developed so far, but the synthesis of most carbohydrate aminoalcohols is to be that glucosamine, xylose are synthetic (for example see Daniel P.G, William P.H, Benjamin G.D.Carbohydrate-derived Aminoalcohol ligands for asymmetric Reformatsky reacti-ons[J]. Tetrahedron: Asymmetry, 2005(16): 213-221; Eva R, Oscar P, Montserrat D. Modular Furanoside Phosphite-Phosphoroamidites, a Readily Available Ligand Library for Asymmetric Catalyzium Palladium Reactions.Origin of Enantioselectivity[J].Adv.Synth.Catal, 2009(351):1648-1670), and the protection of hydroxyl group is 4,6-O-benzyl protection (see for example Spencer K, Paivi J.K, Shashi S , T.G.et.al, Amino Alcohol and Amino Sugar Synthesis by Benzoylcarbamate Cyclization[J].J.Org.Chem, 1990(55):5700-5710), and N, O ligands synthesized from fructose were also synthesized (see for example Huang HM, Chen HL, Hu XQ, et.al.Structuralprobing of D-fructose derived ligands for asymmetric addition of diethylzinc to aldehydes [J]. Tetrahedron: Asymmetry, 2003 (14): 297-304), but with Fructose is the β-aminoalcohol of the present invention that is synthesized as raw material but there is no report

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • D-fructopyranose derived saccharide beta-alkamine and synthesis method thereof
  • D-fructopyranose derived saccharide beta-alkamine and synthesis method thereof
  • D-fructopyranose derived saccharide beta-alkamine and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0029] combine figure 1 , the synthetic method of the carbohydrate β-amino alcohol derived from D-fructose of the present invention, the steps are as follows:

[0030] Step 1: Preparation of 3-O-benzyl-1,2:4,5-bis-O-(1-methyl)ethylene-β-D-fructopyranose, that is, this part includes two steps:

[0031] The first step, the preparation of 1,2:4,5-bis-O-(1-methyl)ethylene-β-D-fructopyranose, various monosaccharides have been catalyzed by acid in this field, Hydroxyl protection to generate diacetonylidene (herein acetonylidene refers to methylene dioxy) technology, including concentrated sulfuric acid catalysis, phosphoric acid catalysis, iodine catalysis, concentrated sulfuric acid catalysis is used in this field, that is, at room temperature, in acetone solution Add concentrated sulfuric acid dropwise. When the amount of concentrated sulfuric acid relative to D-fructose is 0.3-0.4 equivalent, then add D-fructose to the system. After the reaction, add sodium hydroxide solution an...

Embodiment 1

[0053] 1,2: Preparation of 4,5-bis-O-(1-methyl)ethylene-β-D-fructopyranose 1

[0054]

[0055] Add 600mL of acetone to a 1L four-neck flask, add 3mL (0.0553mol) of concentrated sulfuric acid dropwise at room temperature, add 30.6g (0.167mol) of D-fructose at one time, stir at room temperature for 2 hours, and drop 84mL of NaOH solution at 0°C to end the reaction. When the system was light yellow, a large amount of solids were formed. Filtration and concentration gave a yellow solid, 200mLCH 2 Cl 2 , 400mL water wash, water phase with 2 × 200mLCH 2 Cl 2 Extract, combine the organic phases, wash with 2×150mL water, 2×150mL saturated sodium chloride solution successively, Na 2 SO 4 Dry, filter, and concentrate to obtain a light yellow solid, recrystallize from 100 mL petroleum ether, filter, and dry to obtain a white solid 1,2:4,5-bis-O-(1-methyl)ethylene-β-D-pyridine Fructose (67% yield).

Embodiment 2

[0057] 1,2: Preparation of 4,5-bis-O-(1-methyl)ethylene-β-D-fructopyranose 1

[0058] According to the operation of Example 1, the amount of concentrated sulfuric acid was changed to 2.7mL (0.0501mol), and its productive rate was 59%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses D-fructopyranose derived saccharide beta-alkamine and a synthesis method thereof. The general formula of the D-fructopyranose derived saccharide beta-alkamine is shown as the specification, wherein R1 and R2 represent same or different substituent groups which are at least one of lower alkyl of straight-chain alkane or branched alkane with 1 to 4 hydrogen atoms and carbon atoms and aroyl; R3, R4 and R5 are chosen from hydroxy, alkoxy, aryl alkoxy and acyl respectively; and when R3 or R5 is alkoxy, aryl alkoxy or acyl, the two other groups are not hydroxy at the same time and are methylene dioxyl. The new compound can be applied in the fields of materials, medicaments, fine chemical industry, asymmetric catalysis and the like. The synthesis method has the advantages of cheap and readily available raw materials, simple operation and mild reaction condition.

Description

technical field [0001] The invention belongs to the technical field of sugar chemical synthesis, in particular to a sugar β-amino alcohol derived from D-fructose and a synthesis method thereof. Background technique [0002] β-Amino alcohol contains O atoms and N atoms with good coordination ability, which can form complexes with various elements, thus becoming a catalyst with good performance. They are widely used in various fields of national production, including materials, medicine, fine chemicals and asymmetric catalysis. In the field of asymmetric catalysis, it is mainly used as a chiral source of metal chiral ligands and chiral auxiliary agents, and is used to catalyze asymmetric metal alkylation reactions of carbonyl groups, asymmetric Reformatsky reactions, asymmetric reductions, etc. It can be seen that the application of β-amino alcohol is very extensive. Since D-fructose is an optically pure compound that exists in abundance in nature, has multiple chiral center...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07H9/04C07H9/02C07H1/00B01J31/02C07B53/00
Inventor 方志杰李龙霞姜宇华
Owner NANJING UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com