Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for preparing 2-deoxy-N-phenyl pentosamine

A technology of phenylpentosamine and p-toluenesulfonyl, which is applied in the field of preparation of 2-deoxy-N-phenylpentosamine, which can solve the problems of high environmental protection pressure, high production cost and instability, and achieve the reduction of steps and cost, reduce production cost, low cost effect

Inactive Publication Date: 2011-04-13
ZHEJIANG NHU CO LTD
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many synthetic methods for 2-deoxy-N-phenylpentosamine. D-erythrose or D-arabinose is used as the starting material, and special reagents such as mercury are needed. The pressure on environmental protection is very high, and the production cost is high. The resulting product is not easy to purify; with 2,3-O-isopropylidene-D-glyceraldehyde as the starting material, the obtained product cannot guarantee the chirality requirement of C. If the chiral selectivity of C is to be improved, the production must be greatly increased cost
However, because cyclohexanone is a cyclic compound, it is easy to open the ring and is unstable, so that its protective effect on the hydroxyl group on glucose is affected, and the yield of the compound is low; the boiling point of cyclohexanone is high, resulting in difficulties in the recovery of cyclohexanone. The unit consumption is high, the production cost is high, and the price of cyclohexanone raw material is also high

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 preparing 2-deoxy-N-phenyl pentosamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] In a 500ml four-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, add 18.0g (0.1mol) of D-glucose (II), add 180ml of acetone and stir evenly, add 0.3ml of concentrated sulfuric acid dropwise, and then add 45.0ml of copper sulfate g (0.28mol), stirred and reacted at 30-50°C for 20 hours, filtered, and the filtrate was adjusted to alkaline with concentrated ammonia water, then filtered, and the filtrate was concentrated to dryness under reduced pressure at <40°C to obtain 1, 2, 5 , 6-bis-oxy-isopropylidene-α-D-glucose (III): 21.5 g, melting point: 94-98°C, yield: 82%.

Embodiment 2

[0017] In a 250ml four-necked flask equipped with a stirrer and a thermometer, add 21.5g of 1,2,5,6-bis-oxygen-isopropylidene-α-D-glucose (III), add 75ml of toluene, triethylamine 15ml and 12.8g p-toluenesulfonyl chloride, stirred at 5-10°C for 1.5 hours, then adjusted to acidity with concentrated hydrochloric acid, stirred, left to stand for layers, discarded the water layer, collected the organic layer, and reduced to <60°C Concentrate under reduced pressure to remove toluene and water to obtain 1,2,5,6-bis-oxy-isopropylidene-3-oxo-p-toluenesulfonyl-α-D-glucose (IV): 24.8g, melting point: 118~ 120°C, yield: 85%.

Embodiment 3

[0019] In a 250ml four-necked flask with a stirrer and a thermometer, add 21.5g 1,2,5,6-bis-oxygen-isopropylidene-α-D-glucose (III), add toluene 75ml, pyridine 12ml and 12.8g of p-toluenesulfonyl chloride, stirred at 5-10°C for 2 hours, then adjusted to acidity with concentrated hydrochloric acid, stirred, left to stand for layers, discarded the water layer, collected the organic layer, concentrated under reduced pressure at <60°C Remove toluene and water to obtain 1,2,5,6-bis-oxy-isopropylidene-3-oxo-p-toluenesulfonyl-α-D-glucose (IV): 24.2g, melting point: 117~119℃ , Yield: 83%.

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 preparing 2- deoxidation- N- phenyl pentoamine. The current method employs nadone and glucose to protect hydroxy group of glucose under strong sulphuric acid catalytic action, however the nadone is cyclic compound, and not stable, the protective effect for hydroxy group is influenced and the productivity is low and production cost is high. This invention takesD- glucose as raw material, and employs acetone to protect hydroxy group for D- glucose, and acylates 3 position in got product with toluene sulfochloride in basic condition, then removes protective base, saponifies, aminates and gets 2- deoxidation- N- phenyl pentoamine. The invention is characterized by reduced production cost, good protect effect, high productivity of product 1, 2, 5, 6- di- oxygen- isopropyl- alpha- D- glucose.

Description

technical field [0001] The invention relates to a preparation method of sugar amine, in particular to a preparation method of 2-deoxy-N-phenylpentosamine. Background technique [0002] 2-Deoxy-N-phenylpentosamine is an important intermediate in the synthesis of nucleoside drugs, mainly providing deoxyribose sugar groups for nucleoside drugs. There are many synthetic methods for 2-deoxy-N-phenylpentosamine. D-erythrose or D-arabinose is used as the starting material, and special reagents such as mercury are needed. The pressure on environmental protection is very high, and the production cost is high. The resulting product is not easy to purify; with 2,3-O-isopropylidene-D-glyceraldehyde as the starting material, the obtained product cannot guarantee the chirality requirement of C. If the chiral selectivity of C is to be improved, the production must be greatly increased cost. For this reason, Patent Application No. 03116094.8 discloses a preparation method with simple proc...

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 Patents(China)
IPC IPC(8): C07H5/06
Inventor 商志才董金锋俞玉萍
Owner ZHEJIANG NHU CO LTD