dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate

Base Information

• Chemical Name: dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate
• CAS No.: 1311981-35-7
• Molecular Formula: C₂₄H₃₂N₄O₈
• Molecular Weight: 504.54
• Mol file: 1311981-35-7.mol

Synonyms:dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate

Chemical Property of dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate

There total 10 articles about dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 44.0%

C12H14BrNO4 (200344-41-8) + N-(tert-butoxycarbonyl)-L-histidine methyl ester (2488-14-4) → dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate (1311981-35-7)

Guidance literature:

N-(tert-butoxycarbonyl)-L-histidine methyl ester; With magnesium triflate; In acetone; at 50 ℃; for 1h;

C₁₂H₁₄BrNO₄; With dmap; In acetone; at 50 ℃; for 12h; regioselective reaction;

DOI:10.1016/j.tetlet.2014.04.008

Reference yield:

C12H14BrNO4 (200344-41-8) + N-(tert-butoxycarbonyl)-L-histidine methyl ester (2488-14-4) → dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate (1311981-35-7) + dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-?-L-histidino-D-alaninate (1311981-31-3)

Guidance literature:

N-(tert-butoxycarbonyl)-L-histidine methyl ester; With magnesium triflate; In acetone; at 50 ℃; for 1h;

C₁₂H₁₄BrNO₄; In acetone; at 50 ℃; for 12h; Reagent/catalyst; Overall yield = 57 %; regioselective reaction;

DOI:10.1016/j.tetlet.2014.04.008

Reference yield:

C23H30N4O8 + diazomethyl-trimethyl-silane (18107-18-1) → dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate (1311981-35-7)

Guidance literature:

In methanol; at 50 ℃; for 1h;

DOI:10.1016/j.tetlet.2014.04.008

upstream raw materials:

di-tert-butyl dicarbonate

N-(benzyloxycarbonyl)-D-serine

histidine methyl ester hydrochloride

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

Refernces

• 1、 Taylor, Carol M.,De Silva, Samanthi Thabrew. "Synthesis of histidinoalanine: A comparison of β-lactone and sulfamidate electrophiles". . p. 5703 - 5708. Retrieved 2011/09/16.