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Chemical synthesis method of franosterol saponin and its derivative

A technology of furostanol saponin and chemical method, which is applied in the field of chemical synthesis of furostanol saponin and its derivatives, and can solve problems such as limiting the structure-activity relationship of compounds, restricting development and utilization, separation and purification, and partial degradation difficulties

Inactive Publication Date: 2006-04-26
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for 2-OH / OMe furostane-type saponins, because it is usually associated with other saponins and the instability of its structure makes their separation, purification and partial degradation difficult, thereby limiting the structure-activity relationship of this type of compound research, but also restricts its further development and utilization

Method used

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  • Chemical synthesis method of franosterol saponin and its derivative
  • Chemical synthesis method of franosterol saponin and its derivative
  • Chemical synthesis method of franosterol saponin and its derivative

Examples

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Embodiment Construction

[0047] The following examples will help to understand the present invention, but do not limit the content of the present invention.

[0048] Synthetic example

[0049] Synthesis of 26-thiofurostanol saponin VIII:

[0050]

[0051] Reaction scheme 1: Synthesis of 26-position thiofurostanol saponin VIII

[0052] Reagents and conditions: a) 4 Å MS, trimethylsilyl triflate (TMSOTf), CH 2 Cl 2 , rt,; b) oxone, acetone, H 2 O, C 1 -C 6 Halogenated hydrocarbon, rt; c) AlI 3 , CH 3 CN, -40-80°C; d) MeONa, MeOH, CH 2 Cl 2 , -78-40°C; e) NaBH 4 , i-PrOH, CH 2 Cl 2 , rt; f) NaOH, CH 3 OH, H 2 O, 60°C

[0053] (1) Under glycosidation conditions, diosgenin reacts with 2,2,2-trimethylacetyl (Piv)-protected glucose trichloroimide ester donor I to obtain fully protected spirosteroid saponin II; (2 ) II is oxidized with oxone to obtain the product III of the double bond and 16-position oxidation; (3) III and AlI 3 The reaction obt...

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Abstract

The present invention relates to the new process of synthesizing furasteroid saponin and its derivative chemically with C27 helical sterane type sapogenin and various kinds of saccharide as material. The synthesis process includes the following steps: 1. synthesizing completely protected C27 helical steroid saponin through the reaction of C27 helical sterane type sapogenin and acyl radical, alkyl radical or silicon radical protected glycosyl donor; 2. reaction of completely protected helical steroid saponin and oxidant to obtain oxidized product; 3. reaction of oxidized helical steroid saponin and oxyphilic reagent to produce place 26 halogenated saponin derivative; 4. nucleophilic substitution reaction of nucleophilic reagent and the halogenated product to introduce XR3 radical; 5. reducing the place 16 carbonyl radical in saponin selectively with reductant; and 6. eliminating all the protecting radicals to obtain furasteroid saponin and its analog.

Description

technical field [0001] The invention relates to a chemical method for synthesizing furostanol saponin and its derivatives by using spirostanoid saponin and various sugars as raw materials. technical background [0002] 22-OH / OMe furostane type saponin is a kind of saponin whose structure is shown in the figure below. Its structural features are: (1) [0003] Aglycone is C 27 Furanostane-type aglycone; (2) the 5-position can form a double bond with the 6-position (Δ 5 ), can also be the saturated carbon of α / β-H; (3) 12-position substituent Y=O or H, H or OH, H; (4) 22-position OH / OMe / OEt can transform mutually: in MeOH Reflux in / EtOH, OH can be converted to OMe / OEt; [0004] OMe / OEt can be converted to OH by reflux in acetone / water [Hu, K.; Dong, A.; Yao, X.; Kobayashi, H.; Iwasaki, S. Planta Med. 1997, 63, 161-165]; (5)R 1 Can be H, but usually D-glucose (D-Glc), D-galactose (D-Gal), L-rhamnose (L-Rha), D(L)-arabinose (D(L)- Ara) and other monosaccharides and o...

Claims

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Application Information

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IPC IPC(8): C07J71/00
Inventor 李明俞飚
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI