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Other Specialized Reagents

Cbz-D-Prolinol

Category:

Other Specialized Reagents

CAS NO:

72597-18-3

Standard:

BP,USP,

Price Range:

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Main Sales Markets:

North America,Western Europe,Eastern Europe

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Shanghai Sunwise Chemical Co., Ltd.

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Basic Info

CAS Number

72597-18-3

Pharmacopoeia

BP,USP

Grade

Pharmaceutical Grade

Is Manufacturer

YES

Product Description

Pharmaceutical Raw Materials and Intermediates

AI Product Description

*The following content is generated by AI and is for reference only.

Cbz-D-Proline is a crucial chiral building block widely utilized in the pharmaceutical and fine chemical industries for the synthesis of complex organic molecules. Chemically known as N-Carboxybenzyl-D-proline or Cbz-D-Pro-OH, this compound serves as a protected form of D-proline, where the amino group is safeguarded by a benzyloxycarbonyl (Cbz) protecting group. This protection strategy allows chemists to selectively manipulate other functional groups within a molecule without interference from the amine moiety, facilitating multi-step synthetic pathways with high stereochemical fidelity. The molecular formula of Cbz-D-Proline is C13H15NO4, and it carries the CAS registry number 6730-26-9. Its specific stereochemistry, derived from the D-enantiomer of proline, makes it indispensable for producing biologically active compounds that require precise three-dimensional configurations. In practical applications, Cbz-D-Proline is extensively employed in the preparation of peptidomimetics, which are structural analogs of peptides designed to resist enzymatic degradation while retaining biological activity. It acts as a fundamental precursor for synthesizing various drugs, including angiotensin-converting enzyme (ACE) inhibitors used to treat hypertension, as well as potential antiviral and anticancer agents. Furthermore, due to its rigid pyrrolidine ring structure, it is frequently incorporated into catalysts for asymmetric synthesis, enabling the efficient production of single-enantiomer products essential for modern drug development. The presence of the Cbz group also provides versatility; it can be easily removed under mild hydrogenation conditions using palladium on carbon, revealing the free amine for subsequent coupling reactions. This characteristic ensures compatibility with a wide range of reaction conditions found in both academic research laboratories and large-scale industrial manufacturing facilities. Consequently, Cbz-D-Proline remains a staple reagent for researchers aiming to construct sophisticated nitrogen-containing heterocycles and bioactive natural products with defined chirality, ensuring safety and efficacy in final therapeutic applications.