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Method for obtaining cinatrins C3 and C1

A C1-C3, C1-C20 technology, applied in the field of obtaining Cinathelin C3 and C1, can solve the problem of expensive

Inactive Publication Date: 2011-05-18
CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS (CSIC)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the materials used are expensive and various types of protecting groups are used

Method used

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  • Method for obtaining cinatrins C3 and C1
  • Method for obtaining cinatrins C3 and C1
  • Method for obtaining cinatrins C3 and C1

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0176] Preparation of methylrac-(S)-3-(methoxycarbonyl)-2-oxopentadecanoate

[0177]

[0178] MeOH (0.5ml) was added to a suspension of NaH (1.08g, 45.3mmol) in THF (19.5ml) at 0°C. Stir the mixture until it reaches room temperature. Then, methyl myristate (10 g, 41.2 mmol) and dimethyl oxalate (4.87 g, 41.2 mmol) were added. The resulting mixture was heated to reflux for 3 hours. Then, add H at 0°C 2 O (19 mL), the mixture was neutralized with 10% HCl in water. The phases were separated and the aqueous phase was extracted with AcOEt (3 x 10ml). Anhydrous Na for organic phase 2 SO 4 Dry, filter and remove solvent under reduced pressure. The product was purified by chromatographic column (hexane / AcOEt, 20:1) to obtain (8.61 g, yield 64%) methyl rac-(S)-3-(methoxycarbonyl)-2-oxo Pentadecanoate.

[0179] 1 H-NMR (300MHz, CDCl 3 ).δ4.01(1H, t, J=6.9Hz, H-3), 3.88(3H, s, -OCH 3 ), 3.71 (3H, s, -OCH 3 ), 1.88 (2H, m, H-4), 1.24 (20H, m, -CH 2 -), 0.86 (3H, m, -CH ...

Embodiment 2

[0181] Preparation of methyl 2-(tert-butyldimethylsilyloxy)-3-(methoxycarbonyl)-2-pentadecane acrylate

[0182]

[0183] TBDMSOTf (1.84 g, 6.96 mmol) was added to methyl rac-(S)-3-(methoxycarbonyl)-2-oxopentadecanoate (1.90 g, 5.80 mmol) and Et 3 CH of N (1.17 g, 11.6 mmol) 2 Cl 2 (48ml) solution. The mixture was stirred at room temperature for 24 hours. Then, the solvent was removed under reduced pressure. The product was purified by chromatographic column (hexane / AcOEt, 12:1) to obtain (2.09 g, yield 82%) methyl 2-(tert-butyldimethylsilyloxy)-3-(methyl Oxycarbonyl)-2-pentadecenoate.

[0184] IR(NaCl):v 3388, 2943, 2927, 2854, 1738, 1716, 1627, 1432, 1310, 1204, 1129, 1097, 840, 811, 784cm -1 .

[0185] 1 H-NMR (300MHz, CDCl 3 ).δ3.79 (3H, s, -OCH 3 ), 3.71 (3H, s, -OCH 3 ), 2.29 (2H, m, -CH 2 -), 1.32 (20H, m, -CH 2 -), 0.94 (9H, s, tert-BuSi), 0.87 (3H, m, -CH 3 ), 0.17 (6H, s, (CH 3 ) 2 Si).

[0186] 13 C-NMR (75MHz, CDCl 3 ). δ182.3, 168.6, 165....

Embodiment 3

[0190] Preparation of methylrac-(2R,3R)-2-(tert-butyldimethylsilyloxy)-2,3-cyclohydro -3-(Methoxycarbonyl)-pentadecanoate

[0191]

[0192] Add m-CPBA (7.77 g, 45.0 mmol) to methyl 2-(tert-butyldimethylsilyloxy)-3-(methoxycarbonyl)-2-pentadecenoate (9.96 g, 22.5 mmol) of CH 2 Cl 2 (129ml) solution. The mixture was stirred at room temperature for 5 days. Then, celite was added, and the solvent was removed under reduced pressure. The product was purified with a chromatographic column (hexane / AcOEt, 10:1) to obtain (9.96 g, yield 96%) methyl rac-(2R, 3R)-2-(tert-butyldimethylsilane) as a transparent oil oxy)-2,3-epoxy-3-(methoxycarbonyl)-pentadecanoate.

[0193] IR(NaCl):v 3389, 2952, 2928, 2856, 1758, 1462, 1440, 1401, 1362, 1307, 1255, 1199, 1165, 1100, 1004, 843, 785cm -1 .

[0194] 1 H-NMR (300MHz, CDCl 3 ).δ3.76(3H, s, -OCH 3 ), 3.75 (3H, s, -OCH 3 ), 2.07(1H, m, H-4), 1.78(1H, m, H-4), 1.46(2H, m, H-5), 1.24(18H, s broad ,-CH 2-), 0.91 (9H, s, tert-BuSi)...

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Abstract

The invention relates to a method for obtaining cinatrins C1 and C3 and derivatives thereof, comprising the hydroxylation of a compound having formula (III). The invention also relates to the intermediates of this synthesis and to the use thereof in order to obtain cinatrins C1 and C3 and derivatives thereof.

Description

technical field [0001] The present invention relates to the synthesis of cinatrin (cinatrin) C 1 and C 3 The method and the intermediate of the synthesis. The present invention also relates to said intermediate in the synthesis of cinathelin C 1 and C 3 use in . Background technique [0002] Cinatherine C 3 ((3S, 4S, 5R)-3,4-dihydroxy-3-dodecyl-4,5-dicarboxytetrahydro-2-furanone) and C 1 ((3S,4S,5R)-3,4-dihydroxy-5-dodecyl-4,5-dicarboxytetrahydro-2-furanone) belongs to the cinatherine series. [0003] [0004] They were isolated in 1992 from the fungus Circinotrichum falcatisporum Pirozynsky (RF-641 ), isolated from fresh leaves of the Indian rubber tree (Ficus elastica). In 1992, Dr. Itazaki's research group gave the structural description of Cinathelin C3 and C1 [Itazaki, H.; Nagashima, K.; Kawamura, Y.; Matsumoto, K.; Nakai, H.; Terui, Y.J. Antibiot .1992, 45, 38-49.]. They also synthesized cinathelin C from natural compounds extracted from fungi 1 and C 3 o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33C07C69/604C07D303/48C07C69/60C07C391/00C07C69/40
CPCC07C69/716C07B2200/07C07C69/734C07C391/00C07C69/732C07D307/33C07D303/48C07C67/313C07C67/343C07C69/40C07C69/60C07C69/604
Inventor 佩德罗·诺埃达马林路易斯·米格尔·洛萨诺戈蒂洛塞尔吉奥·马罗托金塔纳
Owner CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS (CSIC)