CN105367612A - A total synthesis method of a natural product butyl-2-deoxy-3,6-anhydro-beta-D-arabinofuranoside derived from sauropus rostratus miq. - Google Patents
A total synthesis method of a natural product butyl-2-deoxy-3,6-anhydro-beta-D-arabinofuranoside derived from sauropus rostratus miq. Download PDFInfo
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- CN105367612A CN105367612A CN201410399729.0A CN201410399729A CN105367612A CN 105367612 A CN105367612 A CN 105367612A CN 201410399729 A CN201410399729 A CN 201410399729A CN 105367612 A CN105367612 A CN 105367612A
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Abstract
The invention belongs to the field of chemical synthesis, and particularly relates to a total synthesis method of a natural product butyl-2-deoxy-3,6-anhydro-beta-D-arabinofuranoside derived from sauropus rostratus miq.. The method includes subjecting 2-deoxy-beta-D-arabinopyranose purchased through a commercial route to a plurality of steps of reactions to achieve total synthesis of 2-deoxy-3,6-anhydro-beta-D-arabinofuranoside.
Description
Technical field
The invention belongs to the field of chemical synthesis, relate to the total synthesis method of Leaf of Dragons Tongue origin natural product butyl 2-deoxidation-3,6-dehydration-β-D-R furanoside.
Background technology
Butyl 2-deoxidation-3,6-dehydration-β-D-R furanoside is the hexose compounds of 3, the 5-dehydrations found from Chinese medicine Leaf of Dragons Tongue [SauropusrostratusMiq. (' Longliye ' inChinese)], and structural formula is as follows:
Research finds, this natural product has the pharmacologically active of potential anti-inflammatory, antianaphylaxis and pain relieving.See document (a) Wang, C.H.; Li, W.; Liu, H.L.; Wang, J.; Li, G.Q.; Wang, G.C.; Li, Y.L.Carbohydr.Res.2014,384,99. (b) Zhen, H.S.; Liu, R.; Qiu, Q.; Jiang, J.G.; Yang, Y.Y.Chin.J.Exp.Tradit.Med.Form.2013,19,270. (c) Lin, H.; Lin, B.StraitPharm.J.2011,23,23. etc.
Found by literature research, the content of this natural product in plant is lower, and extraction and isolation is more difficult.In order to expand the source of butyl 2-deoxidation-3,6-dehydration-β-D-R furanoside, we attempt to prepare this natural product by complete synthesis method.
Summary of the invention
The object of the present invention is to provide a kind of natural product butyl 2-deoxidation-3, the total synthesis method of 6-dehydration-β-D-R furanoside, for further with this natural product for primer, structural modification and transformation are carried out to it, finds druggability better there is anti-inflammatory, the pharmacologically active drug candidate of antianaphylaxis and pain relieving provides basis.
For solving the problems of the technologies described above, the invention provides following technical scheme:
With 2-deoxidation-β-D-R pyranose for raw material; first the mixture of butyl 2-deoxidation-α/β-D-R pyranoside and butyl 2-deoxidation-α/β-D-R furanoside is obtained through normal-butyl selective protection hydroxyl; without separation, directly carry out dimethyl tertiary butyl silicon ether and through column chromatography for separation, butyl 2-deoxidation-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside is obtained again to the selective protection of 6 hydroxyls.The hydroxyl of 3,5 obtains butyl 2-deoxidation-3,5-O-di-p-methoxy benzyl-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside by methoxy-benzyl protection.The silicon ether protecting group that this intermediate optionally sloughs 6 again under the effect of tetrabutyl ammonium fluoride obtains primary alconol butyl 2-deoxidation-3,5-O-di-p-methoxy benzyl-β-D-R furanoside.Under 2,6-lutidine and trifluoromethanesulfanhydride anhydride existent condition, above-mentioned primary alconol sulfonylation is obtained butyl 2-deoxidation-3,5-O-di-p-methoxy benzyl-6-O-trifyl-β-D-R furanoside.This intermediate is unstable, directly butyl 2-deoxidation-3 is obtained through intramolecular cyclization reaction in alkali reaction liquid, 6-dewaters-5-O-to after methoxy-benzyl-β-D-R furanoside, slough under the palladium carbon catalytic hydrogenation conditions of 10% 5 to methoxy-benzyl obtain target natural product butyl 2-deoxidation-3,6-dehydration-β-D-R furanoside.
Butyl 2-deoxidation-3 described in synthetic method of the present invention, the synthesis of 6-dehydration-β-D-R furanoside, refer to: the glycosylation reaction being raw material with 2-deoxidation-β-D-R pyranose, solvent is DMF, reaction reagent is propyl carbinol and trifluoracetic acid, temperature of reaction 50 DEG C, the reaction times is 10 little of 24 hours.
Butyl 2-deoxidation-3 described in synthetic method of the present invention, the synthesis of 6-dehydration-β-D-R furanoside, refer to: be raw material with the mixture of butyl 2-deoxidation-α/β-D-R pyranoside and butyl 2-deoxidation-α/β-D-R furanoside 6 is selective silicon etherification reaction, reaction solvent is DMF, reaction reagent can be TBSCl and imidazoles, temperature of reaction is room temperature, and the reaction times is 8 little of 16 hours.
Butyl 2-deoxidation-3 described in synthetic method of the present invention, the synthesis of 6-dehydration-β-D-R furanoside, refer to: be raw material to methoxybenzyl glycosylation reaction with butyl 2-deoxidation-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside, reaction solvent is DMF, reaction reagent is bromobenzyl and sodium hydrogen, temperature of reaction is 0 DEG C, and the reaction times is 2 little of 6 hours.
Butyl 2-deoxidation-3 described in synthetic method of the present invention, the synthesis of 6-dehydration-β-D-R furanoside, refer to: butyl 2-deoxidation-3, the reaction removing silicon ether that 5-O-di-p-methoxy benzyl-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside occurs under the effect of tetrabutyl ammonium fluoride, reaction solvent is tetrahydrofuran (THF), reaction reagent is the tetrahydrofuran solution of the tetrabutyl ammonium fluoride of 1mol/L, and temperature of reaction is room temperature, and the reaction times is 10-20 hour.
Butyl 2-deoxidation-3 described in synthetic method of the present invention; the synthesis of 6-dehydration-β-D-R furanoside; refer to: with butyl 2-deoxidation-3; 5-O-di-p-methoxy benzyl-β-D-R furanoside is trifluoro sulfonylation and the intramolecular cyclization reaction of raw material; reaction solvent is methylene dichloride, and reaction reagent is 2,6-lutidine and trifluoromethanesulfanhydride anhydride; temperature of reaction be-20 DEG C to room temperature, the reaction times is 2 little of 12 hours.
Butyl 2-deoxidation-3 described in synthetic method of the present invention, the synthesis of 6-dehydration-β-D-R furanoside, refer to: with butyl 2-deoxidation-3,6-dehydration-5-O-is the catalytic hydrogenation of raw material to methoxy-benzyl-β-D-R furanoside, reaction solvent is methyl alcohol or dioxane or tetrahydrofuran (THF), reaction reagent is the palladium carbon of 10%, and temperature of reaction is 50 DEG C, and the reaction times is 12 little of 24 hours.
Embodiment
Specific embodiment below can be described in more detail the present invention, but does not limit the present invention in any form.
Embodiment 1
The preparation of butyl 2-deoxidation-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside (3)
By 2-deoxidation-β-D-R pyranose (2g, 12.2mmol), the N of propyl carbinol (40 μ L) and trifluoracetic acid (0.5mL), dinethylformamide (2mL) stirs 10-24 hour under the condition of 50 DEG C, reaction solution is concentrated, the crude product of gained incorporates 20mLN, in dinethylformamide, imidazoles (1.66g is added the condition of 0 DEG C, 24.4mmol) with TBSCl (2.38g, 15.9mmol), after stirring at room temperature 8-16 hour, reaction solution is dropped in frozen water, with dichloromethane extraction, the saturated common salt washing twice of collected organic layer solution, anhydrous sodium sulfate drying, filter, concentrated, (n-hexane/ethyl acetate: 20/1) obtain colorless oil 3 (1.34g is separated through post, 4.0mmol, 33% liang of step).
[α]
D 20＝+46.9(c＝1.0inCHCl
3)；
1H-NMR(300MHz，CDCl
3)：δ5.19(1H，t，J＝4.3Hz)，4.49(1H，dd，J＝8.1，4.1Hz)，3.83-3.78(3H，m)，3.66(1H，dd，J＝10.1，4.3Hz)，3.58(1H，dt，J＝9.5，6.7Hz)，3.30(1H，dt，J＝9.5，6.7Hz)，3.03(1H，s)，2.91(1H，s)，2.09(2H，t，J＝4.4Hz)，1.49-1.40(2H，m)，1.22-1.30(2H，m)，0.85-0.83(12H，m)，0.03(6H，s)；
13C-NMR(75MHz，CDCl
3)：103.1，79.1，71.7，70.2，67.3，64.0，41.5，31.2，25.3(C×3)，18.8，17.8，13.3，-5.9，-6.0；IR(neat，cm
-1)：3415，2928，2856，2384，1638，1618，1464，1400，1256，1109，1035，837，779，750；HRMS(ESI)m/zCalcd.forC
16H
34NaO
5Si[M+Na]
+：357.2073，found357.2068.
Embodiment 2
The preparation of butyl 2-deoxidation-3,5-O-di-p-methoxy benzyl-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside (4)
By 3 (1.2g, 3.6mmol) be dissolved in DMF (5ml), under the condition of 0 DEG C, above-mentioned solution is slowly added containing sodium hydrogen (576mg, 14.4mmol, 60%inliquidparaffin) with to methoxy-benzyl chlorine (PMBCl, 1.75mL, in DMF (10mL) solution 13.0mmol), keeping 0 DEG C to stir dropped in frozen water by reaction solution after 2-6 hour, by extracted with diethyl ether, collected organic layer saturated common salt washing twice, anhydrous sodium sulfate drying, filter, concentrated, (n-hexane/ethyl acetate: 20/1) obtain pale yellow oil 4 (1.8g is separated through post, 85%).
[α]
D 20＝-4.1(c＝1.0inCHCl
3)；
1H-NMR(CDCl
3)：δ7.15-7.12(4H，dd，J＝8.5，1.8Hz)，6.77-6.73(4H，dd，J＝8.5，1.8Hz)，5.15(1H，dd，J＝5.5，3.7Hz)，4.69(1H，d，J＝10.7Hz)，4.41(1H，d，J＝11.3Hz)，4.40(1H，d，J＝10.7Hz)，4.28(1H，d，J＝11.3Hz)，4.14(1H，t，J＝4.0Hz)，3.96-3.90(2H，m)，3.82(1H，ddd，J＝8.8，5.4，1.5Hz)，3.712(3H，s)，3.708(3H，s)，3.67(1H，d，J＝5.6Hz)，3.60(1H，dt，J＝9.5，6.6Hz)，3.30(1H，dt，J＝9.5，6.6Hz)，2.23(1H，dd，J＝14.2，5.5Hz)，1.89(1H，ddd，J＝14.2，5.4，3.7Hz)，1.50-1.40(2H，m)，1.30-1.22(2H，m)，0.85-0.83(12H，m)，0.00(6H，s)；
13C-NMR(75MHz，CDCl
3)：158.4(C×2)，128.7，128.6，113.2，113.1，102.9，78.5，77.6，76.8，71.8，70.2，67.3，63.7，54.7(C×2)，38.7，31.3，25.5(C×3)，18.8，17.8，13.4，-5.9(C×2)；IR(neat，cm
-1)：2928，2855，1615，1514，1400，1249，1121，1039，835；HRMS(ESI)m/zCalcd.forC
32H
50NaO
7Si[M+Na]
+：597.3224，found597.3222.
Embodiment 3
The preparation of butyl 2-deoxidation-3,5-O-di-p-methoxy benzyl-β-D-R furanoside (5)
4 (1.0g, 1.7mmol) are dissolved in tetrahydrofuran (THF) (12ml), under the condition of 0 DEG C, in this solution, dropwise add the tetrahydrofuran solution (20mL) of 1.0mol/L tetrabutyl ammonium fluoride.After gained solution at room temperature stirs 10-20 hour, concentration of reaction solution, thin up, is extracted with ethyl acetate.The saturated common salt washing twice of collected organic layer solution, anhydrous sodium sulfate drying, filters, concentrated, is separated (n-hexane/ethyl acetate: 10/1) obtain pale yellow oil 5 (733mg, 1.6mmol, 92%) through post.
[α]
D 20＝+4.1(c＝1.0inCHCl
3)；
1H-NMR(CDCl
3)：δ7.26-7.16(4H，dd，J＝11.2，8.5Hz)，6.88-6.82(4H，d，J＝8.1Hz)，5.25(1H，dd，J＝5.6，3.4Hz)，4.55(1H，d，J＝11.1Hz)，4.50(1H，d，J＝11.3Hz)，4.48(1H，d，J＝11.1Hz)，4.34(1H，d，J＝11.3Hz)，4.24(1H，t，J＝4.0Hz)，4.07(1H，dd，J＝8.0，3.8Hz)，3.95-3.84(2H，m)，3.80-3.78(7H，m)，3.67(1H，dt，J＝9.6，6.6Hz)，3.39(1H，dt，J＝9.6，6.6Hz)，2.35-2.28(1H，ddd，J＝14.2，5.6，1.4Hz)，2.00(1H，ddd，J＝14.2，5.6，3.4Hz)，1.57-1.48(2H，m)，1.38-1.31(2H，m)，0.90(3H，t，J＝7.3Hz)；
13C-NMR(75MHz，CDCl
3)：159.2(C×2)，130.5，130.1，130.0，129.7，129.4，129.3，129.22，129.20，113.9，113.8，103.2，80.3，77.8，76.0，71.9，70.6，67.9，62.6，55.2(C×2)，39.0，31.7，19.3，13.8；IR(neat，cm
-1)：3416，2924，2853，1736，1614，1514，1466，1400，1249，1175，1121，1036，823；HRMS(ESI)m/zCalcd.forC
26H
36NaO
7[M+Na]
+：483.2359，found483.2354.
Embodiment 4
-5-O-is to the preparation of methoxy-benzyl-β-D-R furanoside (7) in butyl 2-deoxidation-3,6-dehydration
Under-20 DEG C of nitrogen protections, toward containing 5 (500mg, 1.09mmol), 2, trifluoromethanesulfanhydride anhydride (1.6mmol) is dropwise added in methylene dichloride (10mL) solution of 6-lutidine (3.3mmol), after gained solution-20 DEG C stirs half an hour, temperature being increased to room temperature continuation stirring dropped in frozen water by reaction solution after 2-12 hour, with dichloromethane extraction, collected organic layer saturated common salt washing twice, anhydrous sodium sulfate drying, filter, concentrated, (n-hexane/ethyl acetate: 10/1) obtain pale yellow oil 7 (336mg is separated through post, 1.04mmol, 96%).
[α]
D 20＝+76.3(c＝1.0inCHCl
3)；
1H-NMR(CDCl
3)：δ7.32-7.29(2H，d，J＝8.7Hz)，6.89-6.86(2H，d，J＝8.7Hz)，5.34(1H，dd，J＝5.2，1.8Hz)，4.77(1H，m)，4.66(1H，d，J＝11.7Hz)，4.54(1H，d，J＝11.7Hz)，4.48(1H，t，J＝4.7Hz)，4.00-3.93(1H，m)，3.80(3H，s)，3.77(1H，dd，J＝6.4，1.8Hz)，3.70(1H，dt，J＝9.7，6.7Hz)，3.59(1H，t，J＝8.7Hz)，3.40(1H，dt，J＝9.7，6.7Hz)，2.26-2.18(2H，ddd，J＝14.3，7.4，1.8Hz)，2.11-2.03(2H，ddd，J＝14.2，5.2，3.2Hz)，1.56-1.49(2H，m)，1.39-1.33(2H，m，)，0.92(3H，t，J＝7.3Hz)；
13C-NMR(75MHz，CDCl
3)：159.4，129.8，129.7，129.3，113.8，105.7，82.1，78.8，78.2，72.2，67.7，67.5，55.2，41.4，31.7，19.3，13.8；IR(neat，cm
-1)：3131，2385，1640，1613，1513，1401，1249，1081，418；HRMS(ESI)m/zCalcd.forC
18H
26NaO
5[M+Na]
+：345.1678，found345.1676.
Embodiment 5
The preparation of 2-deoxidation-3,6-dehydration-β-D-R furanoside (8)
Methanol solution (8ml) hydrogenation containing 10%Pd-C (200mg) is activated half an hour, will containing 7 (150mg, methyl alcohol (4ml) solution 0.47mmol) adds and contains in the methanol solution of Pd-C through overactivation, catalytic hydrogenation 12-24 hour under 50 DEG C of conditions.By gained solution filtering and concentrating, through column chromatography, (n-hexane/ethyl acetate: 30: 1 → 10/1) obtains colorless oil 8 (82mg, 86%).The collection of illustrative plates of gained compound 8 is without document (Wang, C.H.; Li, W.; Liu, H.L.; Wang, J.; Li, G.Q.; Wang, G.C.; Li, Y.L.Carbohydr.Res.2014) report completely the same.
Claims (7)
1. the total synthesis method of Leaf of Dragons Tongue origin natural product butyl 2-deoxidation-3,6-dehydration-β-D-R furanoside, is characterized in that:
With 2-deoxidation-β-D-R pyranose for raw material; first the mixture of butyl 2-deoxidation-α/β-D-R pyranoside and butyl 2-deoxidation-α/β-D-R furanoside is obtained through normal-butyl selective protection hydroxyl; without separation, directly carry out dimethyl tertiary butyl silicon ether and through column chromatography for separation, butyl 2-deoxidation-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside is obtained again to the selective protection of 6 hydroxyls.The hydroxyl of 3,5 obtains butyl 2-deoxidation-3,5-O-di-p-methoxy benzyl-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside by methoxy-benzyl protection.The silicon ether protecting group that this intermediate optionally sloughs 6 again under the effect of tetrabutyl ammonium fluoride obtains primary alconol butyl 2-deoxidation-3,5-O-di-p-methoxy benzyl-β-D-R furanoside.Under 2,6-lutidine and trifluoromethanesulfanhydride anhydride existent condition, above-mentioned primary alconol sulfonylation is obtained butyl 2-deoxidation-3,5-O-di-p-methoxy benzyl-6-O-trifyl-β-D-R furanoside.This intermediate is unstable, directly butyl 2-deoxidation-3 is obtained through intramolecular cyclization reaction in alkali reaction liquid, 6-dewaters-5-O-to after methoxy-benzyl-β-D-R furanoside, slough under the palladium carbon catalytic hydrogenation conditions of 10% 5 to methoxy-benzyl obtain target natural product butyl 2-deoxidation-3,6-dehydration-β-D-R furanoside.
2. butyl 2-according to claim 1 deoxidation-3, the synthetic method of 6-dehydration-β-D-R furanoside, it is characterized in that the synthesis of the mixture of butyl 2-deoxidation-α/β-D-R pyranoside and butyl 2-deoxidation-α/β-D-R furanoside, refer to: the glycosylation reaction being raw material with 2-deoxidation-β-D-R pyranose, solvent is DMF, reaction reagent is propyl carbinol and trifluoracetic acid, temperature of reaction 50 DEG C, and the reaction times is 10 little of 24 hours.
3. butyl 2-according to claim 1 deoxidation-3, the synthetic method of 6-dehydration-β-D-R furanoside, it is characterized in that the synthesis of butyl 2-deoxidation-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside, refer to: be raw material with the mixture of butyl 2-deoxidation-α/β-D-R pyranoside and butyl 2-deoxidation-α/β-D-R furanoside 6 is selective silicon etherification reaction, reaction solvent is DMF, reaction reagent can be TBSCl and imidazoles, temperature of reaction is room temperature, and the reaction times is 8 little of 16 hours.
4. butyl 2-according to claim 1 deoxidation-3, the synthetic method of 6-dehydration-β-D-R furanoside, it is characterized in that butyl 2-deoxidation-3, the synthesis of 5-O-di-p-methoxy benzyl-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside, refer to: be raw material to methoxybenzyl glycosylation reaction with butyl 2-deoxidation-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside, reaction solvent is DMF, reaction reagent is bromobenzyl and sodium hydrogen, temperature of reaction is 0 DEG C, and the reaction times is 2 little of 6 hours.
5. butyl 2-according to claim 1 deoxidation-3, the synthetic method of 6-dehydration-β-D-R furanoside, it is characterized in that butyl 2-deoxidation-3, the synthesis of 5-O-di-p-methoxy benzyl-β-D-R furanoside, refer to: butyl 2-deoxidation-3, the reaction removing silicon ether that 5-O-di-p-methoxy benzyl-6-O-dimethyl tertiary butyl silica-based-β-D-R furanoside occurs under the effect of tetrabutyl ammonium fluoride, reaction solvent is tetrahydrofuran (THF), reaction reagent is the tetrahydrofuran solution of the tetrabutyl ammonium fluoride of 1mol/L, temperature of reaction is room temperature, reaction times is 10-20 hour.
6. butyl 2-according to claim 1 deoxidation-3, the synthetic method of 6-dehydration-β-D-R furanoside, it is characterized in that butyl 2-deoxidation-3, 6-dewaters-5-O-to the synthesis of methoxy-benzyl-β-D-R furanoside, refer to: with butyl 2-deoxidation-3, 5-O-di-p-methoxy benzyl-β-D-R furanoside is trifluoro sulfonylation and the intramolecular cyclization reaction of raw material, reaction solvent is methylene dichloride, reaction reagent is 2, 6-lutidine and trifluoromethanesulfanhydride anhydride, temperature of reaction is-20 DEG C and arrives room temperature, reaction times is 2 little of 12 hours.
7. butyl 2-according to claim 1 deoxidation-3, the synthetic method of 6-dehydration-β-D-R furanoside, it is characterized in that butyl 2-deoxidation-3, the synthesis of 6-dehydration-β-D-R furanoside, refer to: with butyl 2-deoxidation-3,6-dehydration-5-O-is the catalytic hydrogenation of raw material to methoxy-benzyl-β-D-R furanoside, reaction solvent is methyl alcohol or dioxane or tetrahydrofuran (THF), reaction reagent is the palladium carbon of 10%, temperature of reaction is 50 DEG C, and the reaction times is 12 little of 24 hours.
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| CN112794858A (en) * | 2021-04-14 | 2021-05-14 | 中国药科大学 | Preparation method of compound with 3,4-trans-3, 6-anhydro-hexofuranose structure |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107043403A (en) * | 2016-10-11 | 2017-08-15 | 中国药科大学 | One kind is dehydrated the synthetic method of sugared (glycosides) the structure natural products of D arabinofuranosyls with 2 deoxidations 3,6 |
| CN112794858A (en) * | 2021-04-14 | 2021-05-14 | 中国药科大学 | Preparation method of compound with 3,4-trans-3, 6-anhydro-hexofuranose structure |
| CN112794858B (en) * | 2021-04-14 | 2021-06-25 | 中国药科大学 | Preparation method of compound with 3,4-trans-3, 6-anhydro-hexofuranose structure |
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