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Method for preparing optical activity 2,3-dihydroxy teinai hemiacetal derivant

An internal hemiacetal, optically active technology, used in organic chemistry methods, chemical instruments and methods, organic chemistry, etc., can solve the problems of harsh reaction conditions, expensive reagents, and decreased yield, and achieve mild process conditions and optical purity. High, easy-to-operate effects

Inactive Publication Date: 2010-10-13
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction conditions of this method are harsh, the reagents are expensive, and the post-treatment process is very difficult due to the large amount of colloidal aluminum compounds produced, resulting in a decrease in yield, so this method is not suitable for industrial-scale production

Method used

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  • Method for preparing optical activity 2,3-dihydroxy teinai hemiacetal derivant
  • Method for preparing optical activity 2,3-dihydroxy teinai hemiacetal derivant
  • Method for preparing optical activity 2,3-dihydroxy teinai hemiacetal derivant

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Embodiment 1

[0032] Step 1: Preparation of Diethyl L-tartrate [(2R,3R)-3, R=Et]

[0033] Dissolve L-tartaric acid (15g, 0.1mol) in 50ml of absolute ethanol, add 2ml of concentrated sulfuric acid dropwise, and stop the reaction after refluxing for 10h. Carefully add sodium bicarbonate powder until no gas escapes, filter with suction, and filter the filtrate with anhydrous sulfuric acid After drying over sodium and distilling off the solvent under reduced pressure, 18.5 g (90%) of diethyl L-tartrate was obtained as a pale yellow liquid, which was directly used in the next reaction without further purification. [α] D 20 =+8.7 (c=2.6, EtOH); IR(film): v max =3463, 2980, 1742cm -1 ; 1 H-NMR (400MHz, CDCl 3 ): δ=1.33(t, J=7.2Hz, 6H), 3.38(d, J=6.9Hz, 2H), 4.32(q, J=7.2Hz, 4H), 4.55(d, J=6.9Hz, 2H ); 13 C-NMR (100MHz, CDCl 3 ): δ=14.0, 62.4, 72.0, 171.5; MS (ESI) m / z (%): 229 (M+Na + , 100), 207 (M+H + ,2).

[0034] Step 2: Preparation of L-diethyl tartrate dibenzyl ether [(2R, 3R)-4, ...

Embodiment 2

[0041] Similar to Example 1, the difference is that in step one, anhydrous methanol is used to replace absolute ethanol and L-tartaric acid to react to obtain L-dimethyl tartrate [(2R, 3R)-3, R=Me]; in step two Substitute L-diethyl tartrate with L-dimethyl tartrate to obtain L-dimethyl tartrate dibenzyl ether [(2R, 3R)-4, R=Et, R 1 =Bn]; In step 3, replace diethyl tartrate dibenzyl ether with L-dimethyl tartrate dibenzyl ether to obtain (2R, 3R)-2,3-bis(benzyloxy)-1,4-butanedi Alcohol [(2R,3R)-5, R 1 =Bn].

Embodiment 3

[0043] Similar to Example 1, the difference is that in step one, anhydrous benzyl alcohol is used to replace absolute ethanol and L-tartaric acid to react to obtain L-dibenzyl tartrate [(2R, 3R)-3, R=Bn]; step two Use L-dibenzyl tartrate to replace L-diethyl tartrate to obtain L-dibenzyl tartrate dibenzyl ether [(2R, 3R)-4, R=R 1 =Bn]; Substitute diethyl tartrate dibenzyl ether with L-dibenzyl tartrate dibenzyl ether in step 3 to obtain (2R, 3R)-2,3-bis(benzyloxy)-1,4-butanedi Alcohol [(2R,3R)-5, R 1 =Bn].

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Abstract

The invention discloses a making method of 2, 3-dihydroxy butyl inner hemiacetal derivative with optical activity as chiral intermediate, which comprises the following steps: preparing tartrate ester (3); making tartrate ester (4) protected by alkyl or benzyl or silicon as R1; making 1, 4-butanediol (5); making 2,3-dihydroxy dihydroxy butyl inner hemiacetal derivative (1) under mild synthesizing technique and easy operation with high receiving rate. The invention improves the optical purity of the product, which is a convenient, economic and high-effective product.

Description

technical field [0001] The invention relates to a class of chiral intermediates, in particular to a preparation method of an optically active 2,3-dihydroxybutyrolactal derivative (1). Background technique [0002] Optically active 2,3-dihydroxybutyrolactal and its derivatives (1) are versatile chiral intermediates widely used in pharmaceutical synthesis, natural products, and asymmetric synthesis. The existing optically active 2,3-dihydroxybutyrolactone synthesis method is mainly through the reduction of protected optically active 2,3-dihydroxyγ-butyrolactone with diisopropylaluminum hydride at low temperature (Gypser, A.; Flasche, M.; Scharf, H.D., J.Chem.Soc.Perkin.Trans.1, 1997, 1013; Iida, H.; Yamazaki, N.; Kibayashi, C., J.Org Chem., 1986, 51, 1069). The reaction conditions of this method are harsh, the reagents are expensive, and the post-treatment process is very difficult due to the production of a large amount of colloidal aluminum compounds, which leads to a decr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/20C07B53/00
Inventor 张洪奎曾静
Owner XIAMEN UNIV
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