200344-41-8

Basic information

• Product Name: C₁₂H₁₄BrNO₄
• Synonyms: C₁₂H₁₄BrNO₄
• CAS NO: 200344-41-8
• Molecular Weight: 316.151
• Mol File: 200344-41-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₁₂H₁₄BrNO₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₂H₁₄BrNO₄(200344-41-8)
• EPA Substance Registry System: C₁₂H₁₄BrNO₄(200344-41-8)

Safety Data

• Hazardous Substances Data: 200344-41-8(Hazardous Substances Data)

Upstream product

• 93204-36-5 (R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate 

Downstream Products

• 1311981-35-7 dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate 
• 1311981-31-3 dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-?-L-histidino-D-alaninate 

Relevant articles and documents

Lewis acid facilitated regioselective synthesis of τ-histidinoalanine

τ-Histidinoalanine, with an unusual cross-link between His and Ala, is the central component of theonellamides, a family of bioactive peptidic natural products. Previous syntheses of this residue were plagued with low regioselectivity in the alkylation step. Herein, we report two novel routes to τ-histidinoalanine, involving alkylation of Boc-His-OMe with a serine-derived β-lactone and β-bromoalanine, respectively, as the electrophiles. The use of Mg(OTf)2 as a catalyst was found to be essential to ensure high regioselectivity for the τ-isomer, presumably due to the formation of a six-membered ring chelation involving the π-nitrogen atom of histidine.