Weinreb Linker

Weinreb Linker contains a stabilized N-methoxy-N-methylamide motif providing controlled reactivity toward acyl-transfer mechanisms. Researchers employ it for constructing complex peptide conjugates and studying nucleophilic addition pathways. The linker supports predictable intermediate formation and structural precision. Its stability enhances synthetic flexibility.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Weinreb Linker(CAS 247021-90-5)

CAT No: R2232

CAS No:247021-90-5

Synonyms/Alias:Weinreb Linker;247021-90-5;3-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methoxy)amino)propanoic acid;N-Fmoc-N-methoxy-3-aminopropionic acid;3-[9H-fluoren-9-ylmethoxycarbonyl(methoxy)amino]propanoic acid;beta-Alanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methoxy-;DTXSID80444185;3-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}(METHOXY)AMINO)PROPANOIC ACID;SCHEMBL1274753;DTXCID20395006;Weinreb Linker (N-FMOC-N-methoxy-3-aminopropionic acid);MFCD01861163;AKOS015896021;CS-W009291;HY-W008575;AC-32004;AS-17699;DA-56142;O10855;EN300-1699395;3-(((9H-fluoren-9-yl)methoxy)carbonyl)propanoic acid;3-{[(9H-FLUOREN-9-YLMETHOXY)CARBONYL](METHOXY)AMINO}PROPANOIC ACID;

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cGMP Peptide
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M.F/Formula
C19H19NO5
M.W/Mr.
341.4
Sequence
Three Letter Code:Fmoc-N(OMe)bAla-OH

Weinreb Linker is a specialized organic reagent widely recognized in synthetic chemistry for its pivotal role in facilitating the formation of Weinreb amides. As a functionalized chemical intermediate, it enables precise control over carbonyl compound transformations, particularly in the context of complex molecule assembly. Its unique structural properties, featuring a methoxy-N-methylamide moiety, allow for selective acylation reactions and the prevention of over-addition in organometallic processes. Weinreb Linker's versatility and reliability have established it as an indispensable tool for researchers engaged in advanced organic synthesis, natural product derivatization, and medicinal chemistry investigations.

Synthetic Methodology Development: Weinreb Linker is extensively utilized in the development of novel synthetic routes for the construction of ketones and aldehydes from carboxylic acid derivatives. Its ability to form stable Weinreb amides provides chemists with a robust platform for the introduction of carbonyl functionalities via nucleophilic addition reactions. The linker's predictable reactivity streamlines multi-step synthesis, enabling efficient incorporation of functional groups and facilitating retrosynthetic planning for complex targets.

Selective Acylation Reactions: In organic synthesis, the reagent is employed to achieve highly selective acylation, minimizing side reactions and ensuring the formation of mono-addition products. By forming Weinreb amides, researchers can generate intermediates that react with organolithium or Grignard reagents to yield ketones without risk of over-addition to alcohols. This selectivity is particularly valuable for the preparation of sensitive or multifunctional molecules, where control over chemoselectivity is paramount.

Natural Product Synthesis: The linker plays a critical role in the total synthesis of natural products, where the precise installation of carbonyl groups is often required at specific stages. Its application enables the stepwise assembly of complex molecular architectures, supporting the introduction of key functional groups with high fidelity. The controlled reactivity of Weinreb amides derived from the linker aids in overcoming synthetic challenges associated with polyfunctional intermediates, contributing to the efficient synthesis of structurally intricate compounds.

Medicinal Chemistry and Drug Discovery: In pharmaceutical research, Weinreb Linker is valued for its contribution to the synthesis of advanced intermediates and building blocks used in the design of bioactive molecules. Its incorporation into synthetic schemes facilitates the rapid generation of compound libraries, allowing medicinal chemists to explore structure-activity relationships and optimize lead candidates. The linker's compatibility with a wide range of functional groups enhances its utility in the preparation of diverse scaffolds relevant to drug discovery efforts.

Analytical and Mechanistic Studies: Researchers also employ the linker in mechanistic studies aimed at elucidating the pathways of carbonyl addition reactions. Its well-characterized behavior and predictable transformations make it a useful probe for investigating the kinetics and selectivity of organometallic reagents. Insights gained from such studies inform the rational design of new reagents and methodologies, advancing the broader field of synthetic organic chemistry.

Through these varied applications, Weinreb Linker has become an essential reagent for chemists seeking precision, efficiency, and control in the synthesis of complex molecules. Its unique functional attributes and proven reliability underpin its widespread adoption in both academic and industrial research environments.

InChI
InChI=1S/C19H19NO5/c1-24-20(11-10-18(21)22)19(23)25-12-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,17H,10-12H2,1H3,(H,21,22)
InChI Key
ROUNCJXPHYHPTH-UHFFFAOYSA-N

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