L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-propenyl ester

Base Information

• Chemical Name: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-propenyl ester
• CAS No.: 160788-63-6
• Molecular Formula: C17H23NO4
• Molecular Weight: 305.374
• Mol file: 160788-63-6.mol

Synonyms:

Chemical Property of L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-propenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-propenyl ester

There total 5 articles about L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-propenyl ester 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: 100.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + allyl bromide (106-95-6) → 2-tert-butoxycarbonylamino-3-phenylpropionic acid allyl ester (160788-63-6)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 15h;

DOI:10.1016/j.tet.2004.12.009

Reference yield: 98.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + allyl alcohol (107-18-6) → 2-tert-butoxycarbonylamino-3-phenylpropionic acid allyl ester (160788-63-6)

Guidance literature:

With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime; In water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1021/ol3022337 DOI:10.1021/ol3022337

Reference yield: 91.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + diallyl dicarbonate (115491-93-5) → 2-tert-butoxycarbonylamino-3-phenylpropionic acid allyl ester (160788-63-6)

Guidance literature:

With dmap; In tetrahydrofuran; for 0.0833333h;

DOI:10.1055/s-1994-25638

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

diallyl dicarbonate

allyl alcohol

allyl bromide

Downstream raw materials:

H-Phe-O-allyl hydrochloride

N-tert-butoxycarbonyl-L-phenylalanine

L-phenylalanine allyl ester

C₄₀H₅₂N₄O₁₀

Refernces

• 1、 Lang, Simon B.,O'Nele, Kathryn M.,Douglas, Justin T.,Tunge, Jon A.. "Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms". supporting information. p. 18589 - 18593. Retrieved 2016/01/25.
• 2、 Treder, Adam P.,Tremblay, Marie-Claude,Yudin, Andrei K.,Marsault, Eric. "Solid-phase synthesis of piperazinones via disrupted ugi condensation". supporting information. p. 4674 - 4677. Retrieved 2015/03/30.