Chiral Pool Synthesis

Chiral pool synthesis is an efficient strategy for the asymmetric synthesis of natural products using cheap and versatile raw materials in nature. Chiral pool synthesis provides the basic framework for many compounds. Carbohydrates, amino acids, terpenoids, and alkaloids are often used as chiral sources due to their high functionality and easy availability. In addition to serving as building blocks in total synthesis, chiral pools have also been used to produce asymmetric catalysts, chiral protecting groups, and chiral resolution reagents. BOC Sciences is committed to using cheap and easy-to-obtain natural products as chiral pool raw materials to support the asymmetric total synthesis of various active natural products. We offer a full range of chiral compound development, scale-up and contract manufacturing services from grams to tons. Our vision is to deliver our customers with an exceptional experience, with scientific collaboration at the core setting new standards of cooperation for the pharmaceutical industry, materials chemistry and biological sciences.

Our Custom Synthesis Services

At BOC Sciences, we have extensive chiral compound development and synthesis capabilities. We provide comprehensive support services from raw material screening, synthetic route design to process optimization and quality verification. We have well-equipped expert teams and advanced instrumentation facilities to support the most complex and challenging small molecule synthesis needs.

• Amino Acids

There are 19 common amino acids in the chiral carbon pool, and almost all amino acids exist in two enantiomerically pure forms. Therefore, chiral pool synthesis strategies are often used to plan synthetic routes to produce either enantiomers of the desired target molecules, which makes amino acids extremely valuable and useful in asymmetric synthesis. (S)-amino acids are very common in nature, so they are relatively cheap. (R)-amino acids are mainly obtained from racemates by chiral resolution. In addition, most synthesis-related α-amino acids are also available on the market in the form of ester and N-Boc protected derivatives.

• Carbohydrates

Since carbohydrates can be transformed into corresponding carbon rings, the practicality of using carbohydrates as chiral pools will be greatly enhanced. It is promising to use carbohydrates as components of chiral pools to synthesize complex compounds in optically active forms. Taking D-glucose as an example, it can be easily and selectively converted into pyranose 1, furanose 2, pyranoside 3, gluconolactone 4, tri-O-acetyl-D-glucal 5, and bicyclic derivative 8. Acyclic compounds 6 or 7 can also be obtained by dithioacetal formation or reduction (Fig. 1). The main advantages of carbohydrates as chiral pools are:

• Ready availabibility
• High optical purity (typically 100% ee)
• Presence of polyhydroxyl and carbonyl groups with defined stereochemistry that would be utilized for further transformations
• Availability in various cyclic and acyclic forms, and chain lengths
• Possibility of stereoselective transformations in conformationally rigid ring systems

• Terpenes

Abundant chiral terpene building blocks (i.e., chiral pool terpenes) have long been the starting point for the chemical synthesis of complex natural products, including many terpenes themselves. As cheap and versatile starting materials, these compounds continue to influence modern synthetic chemistry. Since many terpenes are liquids or oils, they cannot be directly crystallized to enantiomeric purity. Furthermore, even if the terpene starting material has a high enantiomeric excess, it may only be available as one enantiomer. Generally, chiral pool terpene synthesis is affected by three main factors:

• The current availability of the starting terpene building blocks
• The current state of the art in synthetic methodology
• The creativity of the practitioner

Our Chiral Pool Raw Materials

Equipments

BOC Sciences has many years of experience and superb technology in the field of chiral synthesis. We can not only provide customers with high-quality chiral synthesis services, but also provide customers with mature chiral analysis technology services. We will wholeheartedly provide you with high-quality comprehensive solutions for chiral analysis.

• High performance liquid chromatography (HPLC)
• Supercritical fluid chromatography (SFC)
• Gas chromatography (GC)
• Capillary electrophoresis (CE)
• Nuclear magnetic resonance spectroscopy (NMR)

Our Highlights

With a complete chemical synthesis manufacturing system, BOC Sciences focuses on each development stage of candidate chemical synthesis. We have the ability to provide the development and customized synthesis solutions of chiral macrocyclic, polycyclic and heterocyclic compounds according to your needs. In addition to custom synthesis, we also provide analysis and process amplification support services. If you are interested in our chiral pool synthesis, please contact us for more information.

Chiral Resolution Techniques by High Performance Liquid Chromatography (HPLC)

Chiral Drugs and Intermediate Resolution Technologies

Determination Techniques for Absolute Configuration of Chiral Compounds

Mechanism of Liquid Chromatographic Resolution of Chiral Compounds