Convenient synthesis method of methylprotodioscin

A technique for the synthesis of methyl protodiosgenin, which is applied in the fields of steroids and organic chemistry, can solve the problems that the synthesis of methyl protodiosgenin has not been reported, and achieve the effect of cheap price and abundant resources

Inactive Publication Date: 2011-09-28
YUNNAN UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, the synthesis of methyl protodiosgenin has not been reported. How to synthesize methyl protodiosgenin concisely and efficiently using high-yield and cheap raw materials has attracted widespread attention from synthetic workers.

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
  • Convenient synthesis method of methylprotodioscin
  • Convenient synthesis method of methylprotodioscin
  • Convenient synthesis method of methylprotodioscin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0026] Step 1, Synthesis of 26-chloro-3β-hydroxyl-16β-acetoxy-5-cholesten-22-one 2

[0027] 11.0g (20mmol) compound 1 and 5.52g (40mmol) K 2 CO 3Place in 150 mL of a mixed solution of tetrahydrofuran and methanol (v:v=1:1), stir at room temperature, and monitor by TLC until the reaction is complete. The reaction takes about 3 hours. After the reaction is completed, add an appropriate amount of ethyl acetate and wash with saturated brine. The organic phase After drying with anhydrous sodium sulfate and removing the solvent under reduced pressure, 9.6 g of oil was obtained, which was purified by silica gel column chromatography to obtain 8.8 g of white solid compound. The yield was 87.0%.

[0028] Compound 2:C 29 h 45 ClO 4 (M=493.12), m.p: 167-168°C.

[0029] 13 C NMR (CDCl 3 , 75MHz) δ13.3 (C 21 ), 16.8 (C 18 ), 17.6 (C 27 ), 19.4 (C 19 ), 20.8 (CH 2 ), 21.2 (OAc), 27.6 (CH 2 ), 31.4(CH), 31.6(CH 2 ), 31.7 (CH 2 ), 34.9 (CH 2 ), 35.0 (CH), 36.5 (C10), 37.2 (CH...

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

A convenient synthesis method of methylprotodioscin belongs to the organic synthesis technical field. The method comprises the following steps: using the rich and cheap E / F full-ring-opening product of protodioscin, namely 26-choro-3beta,16beta-diacetoxy-22-one-5-cholestene as raw material to perform selective alcoholysis of C3-OAc and protection of C3-OH, then in THF / MeOH mixed solution, using the high selectivity of weak base K2CO3 to close E-ring to form C22-OH, then using methyl iodide to perform methylation to C22-OH, and finally performing a substitution reaction and deprotection of C3-OH. The synthesis of methylprotodioscin is realized in a concise and atom economy manner. The raw material and reagents used in the invention are cheap, the operation is simple, the reaction conditions are mild, the product is easy to separate and purify, the yield is high, especially by using the selective ring-opening reaction and the methylation reaction using the active methylating agent methyl iodide, the construction of furan ring in methylprotodioscin and the methylation of C22-OH can be effectively realized, and by attaching the same or different sugar chains to the C3 and C26 of the methylprotodioscin molecule, methylprotodioscin and multiple analogs can be synthesized. Therefore, the method provides a new synthetic approach for methylprotodioscin and other similar saponins.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. Background technique [0002] Steroidal saponins are a class of oligoglycosides that combine sterol compounds with 27 carbon atoms as aglycones and oligosaccharides. They are widely distributed in nature, mainly concentrated in plants such as Liliaceae, Dioscoreaceae and Agaveaceae, and most concentrated in the genus Dioscorea and Liliaceae. From the structure, it can be divided into spirosterane type, furostane type and cholestane type. Furanostane type saponins are an important class of steroidal compounds, and most of them are disaccharide chain saponins in structure, usually in the aglycon C 3 and C 26 Each position is connected with sugar chains, and its representative compound is methyl protodioscin (methyl protodioscin.fig.1), which was first isolated from fresh roots of Dioscoreaceae in 1974. Methyl protodioscin is usually combined with dioscin Saponins are present together ...

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): C07J71/00
Inventor 朱洪友雷泽胡大伟程水连木晓云温晓江付正启
Owner YUNNAN UNIV
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
Try Eureka
PatSnap group products