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20-(tert-Butoxy)-20-oxoicosanoic acid

CAS: 683239-16-9

Purpose: Common Fragments

Formula: C24H46O4

20-(tert-Butoxy)-20-oxoicosanoic acid
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Product description
Core Upstream Building Block for the C20 Lipid Side Chain of Tirzepatide
The extended half-life of Tirzepatide is achieved through the reversible binding of its C20 fatty acid side chain to serum albumin. This product serves as the hydrophobic carbon-chain precursor at the terminal end of the complete lipid side chain. Featuring a selectively mono-protected dicarboxylic acid structure, it prevents simultaneous coupling of both carboxyl groups and the formation of undesired bis-conjugated by-products. This significantly enhances the coupling selectivity with subsequent Glu-AEEA fragments, minimizes side-chain synthesis impurities, and serves as an indispensable starting material for the industrial-scale production of Tirzepatide lipid side chains.
Orthogonal Acid-Labile Protection with a Unified Deprotection Strategy
Only the distal carboxyl group is protected with an OtBu group, while the free COOH group remains available for site-selective amide coupling. The OtBu protecting group can be removed simultaneously during the final TFA cleavage step together with the tert-butyl ester protecting groups on the Glu and AEEA fragments, enabling a one-step deprotection process for the entire lipid side chain and simplifying downstream manufacturing.
No Pharmacological or Cosmetic Activity
This product is a pure long-chain aliphatic ester intermediate without peptide sequences or pharmacologically active functional groups. It cannot penetrate cell membranes or the skin barrier. Direct injection, oral administration, or topical application may leave residual tert-butyl ester decomposition products that may irritate mucosal tissues. Therefore, it is not intended for pharmaceutical formulations or cosmetic applications.
Universal Hydrophobic Building Block for Long-Chain Lipid-Modified Therapeutics
In addition to Tirzepatide, this intermediate is suitable for the synthesis of C20 fatty acid-modified peptides, ADC hydrophobic linker arms, and lipophilic PROTAC molecules. Its selectively mono-tert-butyl protected design effectively overcomes the challenge of non-selective dual coupling in long-chain dicarboxylic acids, streamlining synthetic routes and reducing purification complexity and production costs for long-chain lipid-modified molecules.
This product is supplied exclusively as an upstream organic synthesis intermediate for pharmaceutical API manufacturing. It is intended solely for peptide side-chain synthesis during pharmaceutical production and is not suitable for direct injection, oral administration, or topical application.
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