Method for preparing stereoselectivity of complete protected 2-amido-6-hydroxyl-4-methyl-8-carbonyl capric acid

A technology of stereoselectivity and carbonyl decanoic acid, which is applied in the preparation of organic compounds, chemical instruments and methods, and preparation of cyanide reactions. Selectivity and other issues, to achieve a good effect of stereoselectivity

Inactive Publication Date: 2009-03-25
OCEAN UNIV OF CHINA
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Problems solved by technology

[0003] However, this preparation method has obvious disadvantages: the chiral raw materials used are too expensive, and the epoxidation reaction has no stereoselectivity, which leads to a mixture of a pair of diastereomers obtained by ring opening of the epoxy ring in the subsequent reaction.
There is no report about the stereoselective preparation method of this amino acid so far

Method used

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  • Method for preparing stereoselectivity of complete protected 2-amido-6-hydroxyl-4-methyl-8-carbonyl capric acid
  • Method for preparing stereoselectivity of complete protected 2-amido-6-hydroxyl-4-methyl-8-carbonyl capric acid
  • Method for preparing stereoselectivity of complete protected 2-amido-6-hydroxyl-4-methyl-8-carbonyl capric acid

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Embodiment Construction

[0008] The preparation method of the fully protected 2-amino-6-hydroxyl-4-methyl-8-carbonyldecanoic acid of the present invention can be obtained by (2S, 4S, 6S)-2-(tert-butoxycarbonyl) amino-6- The preparation of benzyloxy-4-methyl-8-carbonyldecanoic acid methyl ester is specifically described, including the following steps: 1, glutamic acid derivatives are introduced into the Evans chiral prosthetic group, which is divided into four steps and carried out, and the specific steps are as follows Shown:

[0009] In the first step, glutamate is reduced to glutamine:

[0010]

[0011] 0.33mol of N-tert-butoxycarbonylglutamic acid-γ-benzyl ester (compound I in the figure) was dissolved in 1600ml of anhydrous tetrahydrofuran and cooled with an ice-salt bath. Add 56ml of triethylamine, then slowly drop into 35ml of ethyl chloroformate. After 30 min, the ice-salt bath was changed to an ice bath, and after stirring for 30 min, a solution of sodium borohydride (37 g) in methanol (3...

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Abstract

The invention discloses a fully-protective stereoselective preparation method of 2-amino-6-hydroxy-4-methyl-8-carbonyl decanoate, which is characterized in that glutamic acid derivants are taken as raw materials and led to a 4-bit chiral center by asymmetric alkylation controlled by Evans chiral auxiliary, and after auxiliary removing, sulphonic acid ester reductive elimination and silicon-ether protecting group removing, the allyl alcohol derivants are obtained; then the allyl alcohol derivants are stereoselectively led to the 6-bit chiral center by Sharpless asymmetric epoxidation; and then the fully-protective 2-amino-6-hydroxy-4-methyl-8-carbonyl decanoate is prepared by epoxy alcohol halogenation, halogenated epoxy alcohol ring opening, Grignard reaction for extending carbochain, oxidation and methyl esterification.

Description

technical field [0001] The invention relates to a preparation method of amino acid, in particular to a stereoselective preparation method of fully protected 2-amino-6-hydroxyl-4-methyl-8-carbonyldecanoic acid. Background technique [0002] 2-Amino-6-hydroxy-4-methyl-8-carbonyldecanoic acid (AHMOD) is an amino acid with complex structure that widely appears in peptaibol compounds, and is one of the important components in this type of biologically active peptides (see literature : (a) Degenkolb, T. et al. J. Pept. Sci. 2003, 9, 666; (b) Iida, A. et al. Bioorg. Med. Chem. Lett. 1999, 9, 3393; (c) Whitmore, L. et al. Eur. Biophys. J. 2004, 33, 233; (d) Toniolo, C. et al. Cell Mol. Life Sci. 2001, 58, 1179.). Because it contains multiple functional groups and several chiral centers, its chemical synthesis is extremely difficult. According to literature search, there is a literature (El-Hadrami, M.E.et al.Tetrahedron Lett.1991, 32, 3985) reporting the preparation method of this...

Claims

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Application Information

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IPC IPC(8): C07C229/22C07C227/00C07C227/16
CPCY02P20/55
Inventor 李英霞张伟孙甜甜李春霞王鹏
Owner OCEAN UNIV OF CHINA
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