17 alpha, 22-dicarboxy furo compound and its use

A technology of hydroxyfurostate compound and diphenyl, applied in the field of 17α, can solve the problems of exacerbating the shortage of plant resources, affecting the ecological environment, destroying vegetation, etc.

Inactive Publication Date: 2005-02-23
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the annual consumption far exceeds the annual growth of Zhonglou, long-term excavation of wild plants not only aggravates the shortage o

Method used

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  • 17 alpha, 22-dicarboxy furo compound and its use
  • 17 alpha, 22-dicarboxy furo compound and its use
  • 17 alpha, 22-dicarboxy furo compound and its use

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of embodiment 1 compound 2

[0028]

[0029] Preparation of 3α,5α-cyclo-6β-methoxy-17α,20R-furostediol:

[0030] Add 2-5 equivalents of lithium reagent (or Grignard reagent) dropwise into 1 equivalent of steroid lactone 1 in 5 mL of anhydrous THF solution, and prepare furostane compound 3α, 5α-cyclo-6β-methoxy at -20°C - 17α, 20R-Furostanediol 2 (20-90% yield).

[0031] Compound 2a (5 equivalents of lithium reagent, 64% yield)

[0032] 1 H-NMR (300MHz, CDCl 3 )δ: 7.66(m, 4H) and 7.36(m, 6H) (phenyls of TPS), 4.15(dd, 1H, J=4.8, 7.2Hz, H-16α), 3.48(m, 2H, H-26) , 3.32(s, 3H, MeO-), 2.78(dd, 't'like, J=2.4Hz, H-6α), 2.20(q, 1H, J=7.5Hz, H-20), 1.05(s, 9H, t-butyl of TPS), 1.04(s, 3H, H-19), 0.94(d, 3H, J=7.2Hz, H-21), 0.89(d, 3H, J=6.6Hz, H-27 ), 0.86 (s, 3H, H-18), 0.66 (dd, 't'like, J=4.0Hz, H-4β), .0.44 (dd, 1H, J=5.2, 7.9Hz, H-3α) .

[0033] ESIMS: m / z 701 (M + +1).

[0034] Compound 2b (3 equivalents of lithium reagent, 20% yield)

[0...

Embodiment 2

[0046] The synthesis of embodiment 2 compound 3

[0047]

[0048] Preparation of Δ5,6-3β,17α,20R-furosttriol:

[0049] Add 2-5 equivalents of lithium reagent (Grignard reagent) dropwise into 5 mL of anhydrous THF solution of 1 equivalent of steroidal lactone 1, and prepare furostanoid compound Δ5,6-3β,17α,20R-furostan at -20°C Triol 3 (50-89% yield). Compound 3a (R 1 =R 2 =H, ) (5 equivalents of lithium reagent, 50% yield)

[0050] 1 H-NMR (300MHz, CDCl 3 )δ: 7.66 (m, 4H) and 7.36 (m, 6H) (phenyls of TPS), 5.54 (d, 1H, J = 8.4Hz, H-6), 4.20 (dd, 1H, J = 4.8, 7.2Hz , H-16α), 3.48(m, 2H, H-26), 3.44(m, 1H, H-3β).2.24(q, 1H, J=7.5Hz, H-20), 1.05(s, 9H, t-butyl of TPS), 1.104 (s, 3H, H-19), 0.98 (d, 3H, J=7.2Hz, H-21), 0.83 (d, 3H, J=6.6Hz, H-27), 0.80(s, 3H, H-18),

[0051] ESIMS: m / z 673 (M + +1).

[0052] Compound 3b (R 1 = MOM,R 2 = H, R 4 =nBu) (3 equivalents of lithium reagent, 89% yield)

[0053] 1 H-NMR (300MHz, CDCl 3 )δ: 5.57(d,...

Embodiment 3

[0064] The synthesis of embodiment 3 compound 4

[0065]

[0066] (25R)-3α, 5α-cyclo-6β-methoxy-26-tert-butyldiphenylsilyloxy-17α, 20R-furostanediol desilication protecting group: 31mg (0.043mmol) furostanes Compound 2a was dissolved in 2 mL of anhydrous THF. Inject 0.43 mL (0.43 mmol) of 1M TBAF in THF, raise the temperature to ~60°C, and stir the reaction. Cool to room temperature, add 10 mL of water, extract with ethyl acetate, and wash the ester layer with saturated NaHCO 3 and NaCl solution, washed with anhydrous Na 2 SO 4 After drying, it was concentrated under reduced pressure. Add 10mgPPTS and 2mL THF to the obtained crude product, stir at room temperature for 2 hours, concentrate under reduced pressure, and obtain oily form by column chromatography: oily (25R)-3α,5α-cyclo-6β-methoxy-17α-spirosterol 19 17mg (81 %Yield).

[0067] Compound 4

[0068] 1 H-NMR (300MHz, CDCl 3 )δ: 3.93(dd, 't'like, 1H, J=7.6Hz, H-16α), 3.48(dd, 1H, J=3.9, 10.6Hz, H-26α), 3.37(dd...

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Abstract

This invention refers to 17alpha ,22 - dihydroxy Furan Steride compounds and its application. The compound' s structure formula is drawing in right graph, wherein the R1, R2 and R3 = H, C1-10 direct chain, cyclane group or alkenyl , triethylsilyl, dimethyl- tert-butylsilyl-biphenyl-tert-butylsilyl, methoxymethyl or tetrahydropyranyl. R4 = H see right formula a, b, C1-10 direct chain, cyclane group, alkenyl or alkynyl , R5 = C1-10 direct chain or cyclane group, R6 = H, C1-10 direct chain or cyclane group or alkenyl, triethylsilyl, dimethyl- tert-butylsilyl, biphenyl-tert-butylsilyl, methoxymethyl, tetrahydropyranyl. The start materials is diosgenin, which is easy available and cheap. Through F-cyclic degrading, the degradation product' s structure is converted into 17alpha,22 - dihydroxy furan steride compound. The compound again with F-cyclic restructure becomes the sapogenin, which is medicinal value. The process thereof is simple, adapted for industrialized production. It's glycoside of medicinal herbs Chonglou (Paris petiolata bak) sapogenin as one active ingredient, whose synthesis is provided herewith is effectively.

Description

technical field [0001] The invention relates to a 17α, 22-dihydroxyfurostate compound and its application. The 17α, 22-dihydroxyfurostanol compound was obtained by using cheap and easy-to-obtain Diosgenin to degrade the F ring, introduce the 17-position hydroxyl group, and modify the side chain. This kind of compound can be used in the synthesis of pennogenin. The glycoside compound of penetogenin is one of the active components of the medicinal plant --- Pachyphysis, and the invention provides a practical approach for the chemical synthesis of the glycoside compound of penetogenin. Background technique [0002] [0003] The glycoside compound of Pennogenin with a 17-hydroxysteroid spiro ring structure is one of the active ingredients of the medicinal plant—Parina genus. Pennaosides are mainly found in the plant of the genus Polyphylla in the family Yanlingaceae. There are 24 species of this genus in the world, and 19 species in China. It is mainly produced in the south...

Claims

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Application Information

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IPC IPC(8): C07J71/00
Inventor 田伟生王真朱伟明
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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