Methyl or ethyl protodioscin chemical synthesis method

A technology of diosgenin and ethyl yam, applied in organic chemistry, steroids, etc., can solve the problems of limiting structure-activity relationship research, difficulty in separation and purification, and low content

Inactive Publication Date: 2007-08-15
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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Problems solved by technology

The content of methyl protodioscin in plants is usually very low, and it is often symbiotic with other saponins of similar polarity, and it is easily converted into spirosteroid saponin due to the action of enzymes during storage, which makes its separation and purification difficult , thus limiting the study of its structure-activity relationship
Chemical synthesis can solve these problems, however, so far, there is only one report on methyl protodioscin [Cheng, M.S.; Wang, Q.L.; Tian, ​​Q.; Song, H.Y.; Liu, Y. X.; Li, Q. .; Xu, X.; Miao, H.D.; Yao, X.S.; Yang, Z.J.Org.Chem.2003, 68, 3658-60], but there is no synthesis about

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  • Methyl or ethyl protodioscin chemical synthesis method
  • Methyl or ethyl protodioscin chemical synthesis method
  • Methyl or ethyl protodioscin chemical synthesis method

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Embodiment Construction

[0036] The following examples will help to understand the present invention, but do not limit the content of the present invention.

[0037] Synthesis Example 1

[0038] Synthesis of methyl protodioscin:

[0039]

[0040] Reaction formula 1: specific synthetic route and embodiment of methyl protodioscin

[0041] Reagents and conditions: a) 2,2,2-tri-methylacetyl chloride (PivCl), pyridine, room temperature; b) potassium persulfate preparation, acetone / H 2 O / C1-C6 halogenated hydrocarbon; c)III, dehydrating agent, accelerator, CH 2 Cl 2 ; d) (C 1～6 h 3～13 ) 3 SiI, NaI, CH 3 CN; e) NaBH 4 , i-PrOH, f) NaOH, CH 3 OH, H 2 o

[0042] (1) Reaction of dioscin with 2,2,2-tri-methylacetyl chloride (PivCl) in pyridine to obtain fully protected dioscin I; (2) oxidation of dioscin I with oxone to obtain double bond and 16-position oxidized Product II; (3) under glycosylation conditions, oxidation product II reacts with benzoyl (Bz)-protected glucose trisimide ester donor II...

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Abstract

The present invention relates to the simple chemical process of synthesizing methyl or ethyl protodioscin with dioscin as material. The process includes the following steps: 1. protecting trisaccharide chain in dioscin; 2. oxidizing the completely protected dioscin; 3. introducing place 26 glucosyl radical; 4. eliminating protecting epoxy radical; 5. reducing place 16 carbonyl radical selectively with reductant; 6. eliminating all the protecting radicals under alkaline or hydrogenating condition to obtain methyl or ethyl protodioscin.

Description

technical field [0001] The invention relates to a simple and simple chemical synthesis method for synthesizing protodioscin by using diosgenin as a raw material. Furthermore, it is a chemical synthesis method of methyl or ethyl protodioscin. technical background [0002] Methyl protodioscin is a furan steroidal saponin with the structure shown in the figure. Its structural characteristics are: (1) methyl protodioscin is a disaccharide chain furanosteroid saponin with sugar groups at the 3-position and 26-position respectively; (2) the aglycon is 25(R)-5-ene-22 -Methoxy-3β, 26-di-hydroxy-furanosteroids; (3) The 3-glycosyl group is [2-O-α-L-rhamnopyranyl-4-O-α-L-rhamnosyl Sugar pyranyl]-β-D-glucopyranyl (β-D-chacotrisyl); (4) The 26th sugar group is β-D-glucopyranyl. In 1974, Kawasaki et al first reported the methyl protodioscophylla [0003] [0004] Separation and extraction of saponins, structural characterization and its physical and chemical properties (Kawasaki, T...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00
Inventor 李明俞飚
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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