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Chiral Building Blocks

Chiral Building Blocks

BOC Sciences specializes in the synthesis of chiral building blocks and other related services, and supports the preparation of customized building blocks to meet the different needs of customers.

Building block is a term in chemistry used to describe a virtual molecular fragment or a real chemical compound whose molecules possess reactive functional groups. As for chiral building blocks, they are valuable intermediates in the syntheses of natural products and pharmaceuticals. With the development of new drugs, it is increasingly necessary to use chiral building blocks for lead optimization, and even in early stages, for the search of efficient compounds. This is mainly because of the fact that almost all biological targets are chiral, and drug-receptor interactions require strict match of chirality.

Example of Chiral Building Blocks at BOC Sciences

Chiral amines (source of chirality-asymmetric synthesis, chiral pool):

Chiral amines are important intermediates in the synthesis of chiral drugs and natural products, and have a wide range of applications in chiral synthesis. Many chiral amines can also be used as chiral auxiliaries and chiral resolution reagents, such as tert-butanesulfinyl aldimine, (R)-(+)-1-Phenylethylamine and so on. The main methods for synthesizing and producing chiral amines are chemical synthesis and enzymatic resolution. The asymmetric catalytic reduction of imines is the most direct and effective method for preparing chiral amine compounds.

Example of catalytic reduction of benzylimin Fig 1. Example of catalytic reduction of benzylimine

Examples of chiral amines Fig 2. Examples of chiral amines

Chiral alcohols are the key chiral building blocks for the synthesis of chiral compounds with high added value. Asymmetric catalytic hydrogenation of carbonyl compounds is an efficient method for the synthesis of chiral alcohols. More than 200 microorganisms can be used as biocatalysts to asymmetrically reduce carbonyl compounds to synthesize chiral alcohols.

Examples of synthesis of chiral alcohols by asymmetric hydrogenation Fig 3. Examples of synthesis of chiral alcohols by asymmetric hydrogenation

Examples of chiral alcohols Fig 4. Examples of chiral alcohols

Chiral carboxylic acids are an important class of chiral building blocks. The preparation of chiral carboxylic acids mainly includes three synthetic methods: asymmetric synthesis, biosynthesis, and resolution of optical isomers.

Example of synthesis of chiral carboxylic acid Fig 5. Example of synthesis of chiral carboxylic acid

Examples of chiral carboxylic acid Fig 6. Examples of chiral carboxylic acid

Example of chiral esters Fig 7. Example of chiral esters

The general methods used to synthesize chiral amides are chiral source synthesis and asymmetric synthesis. For example, using (S)-(+)-1-cyclohexylethylamine or (-)-alpha-phenethylamine as a chiral source, respectively react with methacryloyl chloride to synthesize chiral amide monomers.

Example of amidation reaction Fig 8. Example of amidation reaction

Examples of chiral amides Fig 9. Examples of chiral amides

Chiral amino alcohols are an extremely important class of chiral building blocks and also important chiral ligands. The synthesis methods of chiral amino alcohols are generally asymmetric synthesis methods, mainly including these three methods: reduction or addition of amino acids, reduction of amino acid esters, and azide reduction of ethylene oxide compounds.

Direct reduction of L-proline Fig 10. Direct reduction of L-proline

Examples of chiral amino alcohols Fig 11. Examples of chiral amino alcohols

BOC Sciences has experts with extensive experience in chiral building blocks synthesis services. In the last decades, chiral optically pure building blocks have long been considered as less available than non-chiral building blocks, hence the widespread common opinion is that the non-chiral building blocks are more preferable than chiral building blocks, especially in the early stages of drug development. BOC Sciences would like to refute this opinion by offering a large selection of easily available, optically pure, functionalized chiral building blocks. We can provide various types of chiral building blocks, including chiral secondary and tertiary alcohols, carboxylic acids, amines, alkaloids, lactones, esters and amino alcohols, so that laboratory researchers may discover and build new drug molecules. Moreover, all the synthesized chiral building blocks are analysed for optical purity using modern chromatographic, NMR and other techniques with a quick turnaround time.

Frequently Asked Questions

What are chiral building blocks in organic synthesis?

Chiral building blocks are enantiomerically pure molecules or intermediates used as starting materials in the synthesis of more complex chiral compounds. They are essential for constructing stereochemically defined molecules in pharmaceuticals, agrochemicals, and advanced materials.

What are examples of chiral bases in chemical synthesis?

Examples of chiral bases include sparteine, cinchonidine, and chiral amines derived from amino acids. These compounds are often used as catalysts or auxiliaries to induce stereoselectivity in asymmetric synthesis.

What is an example of a chiral synthesis using building blocks?

One example is the use of (S)-proline as a chiral building block in the asymmetric synthesis of pyrrolidine derivatives, where the stereochemistry of the starting material is transferred to the final product.

Why are chiral building blocks important in research and development?

Chiral building blocks enable the efficient synthesis of molecules with defined stereochemistry, which can have significant effects on biological activity, physical properties, and overall performance in applied research.

What chiral building block services does BOC Sciences provide?

BOC Sciences offers a wide range of chiral building blocks, including amino acids, alcohols, amines, acids, and heterocycles, along with custom synthesis and stereochemistry optimization to meet specific research and development needs.

Expand synthetic capabilities with BOC Sciences chiral building blocks

We provide an extensive range of chiral building blocks with high purity and structural diversity. Our products support asymmetric synthesis, catalysis, and molecular design projects.

Submit your inquiry to request a custom solution.

References

  1. Kaupmann, K., Huggel, K., Heid, J., Flor, P. J., Bischoff, S., Mickel, S. J., ... & Bettler, B. (1997). Expression cloning of GABAB receptors uncovers similarity to metabotropic glutamate receptors. Nature, 386(6622), 239.
  2. Maury, J., Zawodny, W., & Clayden, J. (2017). Stereospecific intramolecular arylation of 2-and 3-pyridyl substituted alkylamines via configurationally stable α-pyridyl organolithiums. Organic letters, 19(3), 472-475.
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