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Preparation method of compound with 3, 4-trans-3, 6-anhydrofuran hexose structure

A technology of hexofuranose and compound, applied in organic chemistry methods, organic chemistry, drug combination and other directions, can solve problems such as inability to form directly

Active Publication Date: 2021-05-14
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When investigating methyl-2-deoxy-α-D-galactopyranoside, it was found that only dimethyl acetal compounds could be formed because the 3- and 4-positions were in trans configuration ( trans ), so the 3,4-trans difuran ring cannot be formed directly

Method used

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  • Preparation method of compound with 3, 4-trans-3, 6-anhydrofuran hexose structure
  • Preparation method of compound with 3, 4-trans-3, 6-anhydrofuran hexose structure
  • Preparation method of compound with 3, 4-trans-3, 6-anhydrofuran hexose structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: D-arabinose (10g, 66.7mmol) was dissolved in 50mL of dry methanol, and chloroacetyl (0.01mL, 0.14mmol) was slowly added dropwise under ice-bath conditions, and the temperature was naturally raised to room temperature after stirring, and then continued Stir for 4 hours, add sodium bicarbonate powder to the reaction solution to adjust the pH value to 7, filter, concentrate under reduced pressure, and separate by silica gel column chromatography (dichloromethane:methanol volume ratio is 50:1) to obtain compound No.1 (10.5g, 64.0 mmol, 96%).

[0032] Dissolve compound NO.1 in dry N,N - Dimethylformamide (DMF) 150mL, stirring, 0 ℃ ice bath for 30min, sequentially add imidazole (11g, 172mmol), tert-butyldimethylsilyl chloride (TBSCl, 12g, 80mmol), after stirring for 10h, add Quenched with ice water, CH 2 Cl 2 (dichloromethane) extracted three times, then washed five times with ice water, washed three times with saturated sodium chloride, concentrated under redu...

Embodiment 2

[0035] Example 2: Dissolve compound NO.2 (8.7g, 31.3mmol) in 80 mL of N,N dimethylformamide, add sodium hydride (60%, 3.8g, 93.9mmol) under ice-water bath conditions, and Stirring under this condition for 30 min, adding benzyl bromide (8.2 mL, 9 mmol), and stirring for 5 h after naturally warming to room temperature. After the reaction was completed, quenched with ice water, extracted three times with a mixed solvent of ethyl acetate:petroleum ether=1:1, after the organic phases were combined, washed three times with ice water, twice with saturated sodium chloride solution, and decompressed Concentrate, and perform silica gel column chromatography (petroleum ether: ethyl acetate = 50:1) to obtain compound NO.3 (13.2 g, 92.3%) as a yellow oil.

[0036] α-anomer: [α] D 25 = -28(c = 2.1 in CHCl 3 ); 1 H-NMR (300 MHz, CDCl 3 ): δ7.51 – 7.25 (m, 10H), 4.79 – 4.53 (m, 5H), 4.25 – 4.10 (m, 2H), 4.10 – 3.98(m, 1H), 3.86 – 3.67 (m, 2H), 3.43 (d, J = 9.2 Hz, 3H), 0.97 (d, J =...

Embodiment 3

[0037] Example 3: Dissolve compound NO.3 (13.2g, 28.8mmol) in 30mL of tetrahydrofuran, add 1M tetrabutylammonium fluoride (9.1g, 28.8mmol), stir at room temperature for 8h, after the reaction, add methanol Quenched, concentrated under reduced pressure, and subjected to silica gel column chromatography (petroleum ether: ethyl acetate = 50:1-10:1) to obtain colorless oily compound NO.4 (8.92g, 90%).

[0038] α-anomer: [α] D 25 = +19.6 (c = 1.5 in CHCl 3 ); 1 H-NMR (300 MHz, CDCl 3 ):δ 7.35 (dd, J = 5.5, 2.3 Hz, 10H), 4.96 (s, 1H), 4.65 – 4.49 (m, 4H), 4.16 (dt, J = 6.6, 3.2 Hz, 1H), 4.01 (dt, J = 8.8, 2.7 Hz, 2H), 3.85 (dd, J =12.0, 2.9 Hz, 1H), 3.66 (dd, J = 11.6, 3.5 Hz, 1H), 3.40 (s, 3H); 13 C-NMR (75MHz, CDCl 3 ): δ138.5, 127.6, 127.7, 127.4, 110.2, 84.0, 82.0, 81.2, 73.3,63.6, 55.8,, 26.3, 25.8; HRMS(ESI) m / z Calcd. for C 25 h 32 NaO 8 [M+Na]+: 367.1603, found 367.1605.

[0039] β-anomer: [α] D 25 = -28 (c = 2.1 in CHCl 3 ); 1 H NMR (300 MHz, CD...

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Abstract

The invention discloses a preparation method of a compound with a 3, 4-trans-3, 6-dehydrated furan hexose structure and a preparation method of the compound with the 3, 4-trans-3, 6-dehydrated furan hexose structure. The method comprises the following steps: carrying out multi-step reaction, carrying out hydrogenation by taking palladium on carbon as a catalyst to remove benzyl, and simultaneously initiating intramolecular hemiacetalation reaction, so as to obtain a compound with a 3, 4-trans-3, 6-dehydrated furan hexose structure.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and relates to a compound with 3,4- trans -The preparation method of the compound of 3,6-anhydrohexfuranose structure. Background technique [0002] Sauropunol E is obtained from Asparagus leaves Sauropus spatusifolius Beille The natural active ingredients extracted from plants, through the analysis of its structure, it is found that it has the extremely rare 3,4- trans -3,6-anhydrohexofuranose skeleton structure. [0003] Through literature research, it is found that the current understanding of 3,4- trans The chemical synthesis method of -3,6-anhydrohexofuranose skeleton has not been reported yet. Foster et al. reported methyl-3,6-anhydro-2-deoxy-α-D-glucopyranoside and methyl 3,6-anhydro-2-deoxy-α-D-galactopyranoside in 1954 Synthesis of glycosides and their corresponding 4-methyl ether derivatives. When investigating methyl-2-deoxy-α-D-galactopyranoside, it was found that only dimethyl...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61P29/00
CPCA61P29/00C07B2200/07C07D493/04
Inventor 谢唯佳王志梅陶文祥
Owner CHINA PHARM UNIV
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