Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing 1,3,4,6-tetraacetyl-L-gulose

A technology of tetraacetyl and gulose, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of high requirements for experimental operators, difficult to scale up production, long synthetic routes, etc., and achieve the synthetic route. Short, easy-to-operate, easy-to-control effects

Inactive Publication Date: 2014-06-11
EAST CHINA NORMAL UNIVERSITY
View PDF2 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Most of these reported synthetic methods have long synthetic routes, require the use of more expensive raw materials or chemical reagents, and have high requirements for experimental operators, making it difficult to achieve scale-up production

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
  • Method for synthesizing 1,3,4,6-tetraacetyl-L-gulose
  • Method for synthesizing 1,3,4,6-tetraacetyl-L-gulose
  • Method for synthesizing 1,3,4,6-tetraacetyl-L-gulose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] 1.1 Preparation of compound Ⅱ

[0044] Dissolve 1.5g of compound I in 15ml of acetone at room temperature, add 1.25ml of concentrated sulfuric acid dropwise after cooling in an ice bath, and stir the reaction mixture at room temperature for 1-2 hours. Add NaHCO to the reaction solution 3 50g of powder, until pH ≥ 7, filtered out the solid, spin-dried the solvent, and crystallized with ethyl acetate to obtain a white solid, namely compound II, 1.56g, yield 85%.

[0045] [a] D 25 +55.3 (c 0.92 CHCl3).

[0046] 1 H NMR (400 MHz, CDCl 3 ) δ 5.99 (d, J = 3.5 Hz, 1H), 4.95 (dd, 4.2, 3.5, 1H), 4.83-4.82 (m, 2H), 4.50 (dd, J = 9.0, 4.2 Hz, 1H), 2.86 (d, J = 9.0 Hz, 1H), 1.53 (s, 3H), 1.36 (s, 3H).

[0047] MS (EI): m / e = 216.

[0048] 1.2 Preparation of compound Ⅱ

[0049] Dissolve 1.5g of compound I in 15ml of acetone at room temperature, add 1.25ml of concentrated sulfuric acid dropwise under ice-bath cooling, and warm the reaction mixture to room temperature an...

Embodiment 2

[0059] 2.1 Preparation of Compound III

[0060] 10.7 g of compound II was dissolved in 50 ml of ethyl acetate, 7 g of silver oxide and 7 ml of benzyl bromide were added at room temperature, and the reaction mixture was stirred overnight at room temperature. The solid in the reaction mixture was filtered off, and the filtrate was concentrated and purified by column chromatography to obtain an oily substance, namely compound III, 13 g, with a yield of 86%.

[0061] [a] D 26 +44.5 (c 0.92, CHCl3).

[0062] 1 H NMR (400 MHz, CDCl 3 ) δ 7.37 (m, 5H), 6.04 (d, J = 3.6 Hz, 1H), 4.92 (s, 2H), 4.86 (dd, J = 4.3, 2.9HZ, 1H), 4.79 (d, J = 3.6 Hz, 1H), 4.71 (d, J = 2.9 Hz, 1H), 4.25 (d, J = 4.3 Hz, 1H), 1.50 (s, 3H), 1.34 (s, 3H).

[0063] MS (EI): m / e=306.

[0064] 2.2 Preparation of Compound III

[0065] 10.7g of compound II was dissolved in 50ml of DMF, 7g of silver oxide and 7ml of benzyl bromide were added at room temperature, and the reaction mixture was stirred at...

Embodiment 3

[0075] 3.1 Preparation of mixture IV

[0076] 1g compound III was dissolved in 8ml CH 2 Cl 2 Cool to -78°C, and slowly add 7.4ml of 1.1M DIBAL-H dropwise to the reaction solution. The reaction mixture was stirred at -40°C for 2 hours, 15ml of saturated sodium potassium tartrate solution was added to the reaction solution, stirred overnight at room temperature, allowed to stand, and separated into layers, the organic phase was separated, dried and purified by column chromatography to obtain an oily mixture IV (poor To isomers) 0.9g, yield 90%, the mixture was directly used in the next reaction.

[0077] 3.2 Preparation of mixture IV

[0078] 1g compound III was dissolved in 8ml CH 2 Cl 2 Cool to -78°C, slowly add 6.8ml of 1.1M DIBAL-H dropwise to the reaction solution. The reaction mixture was stirred at -40°C for 2 hours, 15ml of saturated sodium potassium tartrate solution was added to the reaction solution, stirred overnight at room temperature, allowed to stand, separ...

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 a method for synthesizing 1,3,4,6-tetraacetyl-L-gulose. According to the method, a compound, namely, 1,3,4,6-tetraacetatyl-L-gulose is prepared from glucuronolactone serving as a raw material by performing the steps of acetonide protection, benzyl protection, lactone reduction, hemiacetal hydroxyl protection, acetonide de-protection, lactone reduction, hemiacetal hydroxyl de-protection, acetyl protection and benzyl deprotection. In the method, experience reagents are not used, so that the cost is reduced; involved operation is simple and convenient, conditions are easy to control, and industrial production is easy; the total yield is high, and can be magnified to gram grade and over.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to bleomycin A 2 The technical field of preparation of L-gulose in disaccharide units, more specifically refers to a method for synthesizing 1,3,4,6-tetraacetyl-L-gulose. Background technique [0002] Bleomycin is a class of glycopeptide antibiotics with similar structure produced by Streptomyces verticillium. It can be used for anti-tumor by mediating the oxidative cleavage of DNA and RNA of tumor cells. It is commonly used clinically in Hodgkin's lymphoma Tumors, squamous cell tumors, etc. In addition, because bleomycin can specifically target human and animal tumor cells, it is clinically used as a tumor diagnostic drug. Structurally, the bleomycin molecule consists of a hexapeptide and a disaccharide moiety, where the disaccharide moiety is thought to not only form a molecular cavity to assist the process of oxidative cleavage, but also play an important role in c...

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
IPC IPC(8): C07H13/06C07H1/00
Inventor 吕伟刘新桂车锐罗宇
Owner EAST CHINA NORMAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap 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