A kind of chiral 3-(2-nitroethyl)tetrahydrofuran compound and its preparation method

A technology of hydroxytetrahydrofuran and nitroethyl is applied in the field of chiral 3-(2-nitroethyl)tetrahydrofuran compound and its preparation, and in the field of tetrahydrofuran compound material, which can solve the problem that the synthesis method of 3-substituted tetrahydrofuran compound is rare, and the hand is limited. The application of 3-substituted tetrahydrofuran compounds is difficult to meet the requirements of practical application, and the effect of good application prospect, novel structure and short reaction time is achieved.
CN103755667BActive Publication Date: 2016-01-20杭州三隆新材料有限公司
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
杭州三隆新材料有限公司
Publication Date
2016-01-20

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Abstract

The invention discloses a chiral 3-(2-nitro ethyl) tetrahydrofuran compound and a preparation method thereof. The preparation method specifically comprises the following steps: performing Michael addition reaction on 2-hydroxytetrahydrofuran and nitroalkene by using proline-derived chiral pyrrolidine serving as a catalyst, and performing Et3SiH / BF3.Et2O reduction to remove 2-hydroxyl to obtain the product. According to the chiral 3-(2-nitro ethyl) tetrahydrofuran compound and the preparation method for the same, the compound is novel in structure and high in enantiomeric purity; a plurality of active natural products and medicaments contain tetrahydrofuran structures, so that the compound has high application value in the total synthesis of the natural products and the discovery of new medicaments, and has good application prospect.
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Description

technical field

[0001] The invention relates to a tetrahydrofuran compound material, in particular to a chiral 3-(2-nitroethyl) tetrahydrofuran compound and a preparation method thereof, belonging to the field of organic synthesis. Background technique

[0002] Tetrahydrofuran compounds are a class of important skeleton structures with special medicinal compounds. They are widely found in many natural products and drugs. The most common one is the deoxyribonucleic acid unit in the DNA structure. In addition, many natural products such as five-carbon sugars, Polyether natural products and some lignins contain one or more tetrahydrofuran rings. Clinically used drugs such as antiviral and anticancer nucleoside drugs and antibacterial posaconazole all contain tetrahydrofuran structures. The antiviral drug Amp Navir contains a chiral 3-oxotetrahydrofuran moiety.

[0003] In the prior art, there are many reports on the synthesis of 2-substituted, 2,3-disubstituted, 2,5-disubstitu...

Claims

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