1311981-35-7

Basic information

• Product Name: dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate
• Synonyms: dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate
• CAS NO: 1311981-35-7
• Molecular Weight: 504.54
• Mol File: 1311981-35-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate(1311981-35-7)
• EPA Substance Registry System: dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate(1311981-35-7)

Safety Data

• Hazardous Substances Data: 1311981-35-7(Hazardous Substances Data)

Upstream product

• 98632-91-8 N-(benzyloxycarbonyl)-D-serine-β-lactone 
• 501-53-1 benzyl chloroformate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 200344-41-8 C₁₂H₁₄BrNO₄ 
• 2488-14-4 N-(tert-butoxycarbonyl)-L-histidine methyl ester 
• 93204-36-5 (R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate 
• 4467-54-3 histidine methyl ester hydrochloride 
• 6081-61-4 N-(benzyloxycarbonyl)-D-serine 
• 24424-99-5 di-tert-butyl dicarbonate 

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.