Method for synthesizing chiral methyl 1,3 functional group synthon

Abstract

This invention relates to one kind of chirality methyl side chain contain 1, 3-functional group synthon synthetic method. 4R-4-methyl valerolactone or 4S-4- methyl valerolactone in steroid sapogenines degradation waste liquor is used as initial material, source is fully used and pollution is reduced. This invention provides large scale getting chirality methyl side chain contain 1,3-functional group chiral synthesis building block technique, these block can be used as initial material of making natural generation and medicine that contain chirality methyl. The 1, 3-functional group synthon has following structure characteristics.

Description

technical field [0001] This patent relates to a class of 1,3-functional group synthons with chiral methyl side chains. The compound can be optically pure 2-methyl-3-allyl propanol, optically pure 2-methyl-3-aldehyde Propanol, optically pure 2-methyl-3-hydroxypropanol, and their derivatives. They can be conveniently prepared in large quantities from 4R-4-methylvalerolactone or 4S-4-methylvalerolactone. Such compounds are very useful building blocks for chiral synthesis. Background technique [0002] 1,3-functional synthons with chiral methyl side chains are widely used in organic synthesis and are important intermediates for the preparation of pharmaceuticals and fine chemicals. They have bifunctional groups that can be further extended and can be obtained relatively easily Other chiral synthons (Organic Chemistry, 2003, 23, 1236; Synthesis, 1993, 1029). Due to their importance in the synthesis of bioactive substances and functional materials and their wide range of applic...

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Problems solved by technology

[0003] Bifunctional chiral synthetic building blocks with chiral methyl side chains can be synthesized by asymmetric synthesis techniques. The commonly used methods are by introducing chiral prosthetic groups (Evans reagent, S(R)AMP, etc.) or directly with chiral Substrate reaction (L-tartrate-(E)-crotyl, BINOL-TiX 2 etc.), but the synthesis route of this method is generally longer, and the reagents used are expensive, and generally limited to laboratory gram-scale synthesis; it can also be prepared by biotechnology (such as asymmetric ester hydrolysis of microorganisms, etc.), but this method The yield of a single isomer is relatively low, and the operation is relatively cumbersome; another common method is to use natural products containing chiral methyl groups (natural citronellol, citronellal, glyceraldehyde, malic acid, tartaric acid, Serine, etc.) is an effective method to provide such chiral building blocks on a large scale, but the varieties of such chiral building blocks currently available are limited, too long (C>7) or too short (C=3) The synthesis efficiency of carbon chain is low, which brings unfavorable factors to its application

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