(S)-2-Tert-butoxycarbonylamino-3-(3,4,5-trimethoxy-phenyl)-propionic acid

Base Information

• Chemical Name: (S)-2-Tert-butoxycarbonylamino-3-(3,4,5-trimethoxy-phenyl)-propionic acid
• CAS No.: 477254-82-3
• Molecular Formula: C₁₇H₂₅NO₇
• Molecular Weight: 355.388
• European Community (EC) Number: 896-994-6
• Nikkaji Number: J3.169.420E
• Mol file: 477254-82-3.mol

Synonyms:477254-82-3;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(3,4,5-TRIMETHOXY-PHENYL)-PROPIONIC ACID;SCHEMBL2675114;(2S)-2-{[(tert-Butoxy)carbonyl]amino}-3-(3,4,5-trimethoxyphenyl)propanoic acid;ZVGAWGZORXNQJF-NSHDSACASA-N;Boc-L-Phe(3,4,5-OMe3)-OH;MFCD07372083;EN300-6732094;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(3,4,5-trimethoxyphenyl)propanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-3-(3,4,5-trimethoxyphenyl)propanoic acid

Chemical Property of (S)-2-Tert-butoxycarbonylamino-3-(3,4,5-trimethoxy-phenyl)-propionic acid

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 355.16310214
• Heavy Atom Count: 25
• Complexity: 435

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC(=C(C(=C1)OC)OC)OC)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC(=C(C(=C1)OC)OC)OC)C(=O)O

Technology Process of (S)-2-Tert-butoxycarbonylamino-3-(3,4,5-trimethoxy-phenyl)-propionic acid

There total 12 articles about (S)-2-Tert-butoxycarbonylamino-3-(3,4,5-trimethoxy-phenyl)-propionic acid 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: 92.0%

(S)-tert-butyl (1-hydroxy-3-(3,4,5-trimethoxyphenyl)propan-2-yl)carbamate (1426447-10-0) → (S)-2-((tert-butoxycarbonyl)amino)-3-(3,4,5-trimethoxyphenyl)propanoic acid (477254-82-3)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In water; acetonitrile; at 20 ℃; for 5h;

DOI:10.1016/j.tet.2013.02.079

Reference yield: 87.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl (S)-2-acetamido-3-(3,4,5-trimethoxyphenyl)propanoate → (S)-2-((tert-butoxycarbonyl)amino)-3-(3,4,5-trimethoxyphenyl)propanoic acid (477254-82-3)

Guidance literature:

di-tert-butyl dicarbonate; methyl (S)-2-acetamido-3-(3,4,5-trimethoxyphenyl)propanoate; With dmap; In tetrahydrofuran; at 75 ℃; for 3h;

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 3h;

DOI:10.1002/anie.201901056

Reference yield: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + 3,4,5-trimethoxy-L-phenylalanine (18652-97-6) → (S)-2-((tert-butoxycarbonyl)amino)-3-(3,4,5-trimethoxyphenyl)propanoic acid (477254-82-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 4h;

DOI:10.1021/jm049660v

upstream raw materials:

di-tert-butyl dicarbonate

3,4,5-trimethoxy-L-phenylalanine

(S)-tert-butyl 4-(3,5-diiodo-4-methoxybenzyl)-2,2-dimethyloxazolidine-3-carboxylate

(S)-tert-butyl 4-(3,5-dibromo-4-methoxybenzyl)-2,2-dimethyloxazolidine-3-carboxylate

Downstream raw materials:

[(S)-1-[(S)-1-(2-hydroxy-4-methoxybenzylcarbamoyl)-2-methylpropylcarbamoyl]-2-(3,4,5-trimethoxyphenyl)ethyl]carbamic acid tert-butyl ester

Refernces

• 1、 Chen, Ruijiao,Liu, Hao,Liu, Xiubing,Chen, Xiaochuan. "An efficient synthesis of l-3,4,5-trioxygenated phenylalanine compounds from l-tyrosine". . p. 3565 - 3570. Retrieved 2013/04/24.