851713-94-5

Basic information

• Product Name: L-Tyrosine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1,1-dimethyl-2-propenyl ester
• CAS NO: 851713-94-5
• Molecular Formula: C33H37NO5
• Molecular Weight: 527.66
• Mol File: 851713-94-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: L-Tyrosine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1,1-dimethyl-2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Tyrosine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1,1-dimethyl-2-propenyl ester(851713-94-5)
• EPA Substance Registry System: L-Tyrosine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1,1-dimethyl-2-propenyl ester(851713-94-5)

Safety Data

• Hazardous Substances Data: 851713-94-5(Hazardous Substances Data)

Upstream product

• 556-82-1 3-methyl-2-buten-1-ol 
• 71989-38-3 Fmoc-Tyr(tBu)-OH 
• 851713-82-1 Fmoc-Tyr(t-Bu)-dimethylpropargyl ester 

Downstream Products

• 71989-38-3 Fmoc-Tyr(tBu)-OH 

Relevant articles and documents

An Optimized Preparation of 1,1-Dimethylallyl Esters and Their Application to Solid-Phase Peptide Synthesis

A one-step preparation of 1,1-dimethylallyl (DMA) esters was optimized for the C-terminal protection of a range of Fmoc-protected amino acids. This preparation is not sensitive to the scale of reaction and affords the corresponding DMA esters in 70-99% yield with high regioselectivity. Additionally, these DMA-protected amino acids were used with the backbone amide linker (BAL) of Albericio and Barany and found to resist diketopiperazine formation during the synthesis of a series of tripeptide esters. C-terminal DMA protection is compatible with the BAL linkage and allows for standard Fmoc-based methods to be used throughout the synthesis.

A convenient, general synthesis of 1,1-dimethylallyl esters as protecting groups for carboxylic acids

(Chemical Equation Presented) Carboxylic acids were converted in high yield to their 1,1-dimethylallyl (DMA) esters in two steps. Palladium-catalyzed deprotection of DMA esters was shown to be compatible with tert-butyl, benzyl, and Fmoc protecting groups, and Fmoc deprotection could be carried out selectively in the presence of DMA esters. DMA esters were also shown to be resistant to nucleophilic attack, suggesting that they will serve as alternatives to tert-butyl esters when acidic deprotection conditions need to be avoided.