N-(tert-Butoxycarbonyl)-L-tyrosyl-D-alanine

Base Information

• Chemical Name: N-(tert-Butoxycarbonyl)-L-tyrosyl-D-alanine
• CAS No.: 71591-34-9
• Molecular Formula: C17H24N2O6
• Molecular Weight: 352.387
• DSSTox Substance ID: DTXSID90545455
• Wikidata: Q82422953
• Mol file: 71591-34-9.mol

Synonyms:71591-34-9;N-(tert-Butoxycarbonyl)-L-tyrosyl-D-alanine;SCHEMBL4024913;DTXSID90545455

Chemical Property of N-(tert-Butoxycarbonyl)-L-tyrosyl-D-alanine

Chemical Property:

• PSA: 131.94000
• LogP: 2.46200
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 352.16343649
• Heavy Atom Count: 25
• Complexity: 480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of N-(tert-Butoxycarbonyl)-L-tyrosyl-D-alanine

There total 6 articles about N-(tert-Butoxycarbonyl)-L-tyrosyl-D-alanine 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: 93.0%

N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanine methyl ester (74392-86-2) → N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanine (71591-34-9)

Guidance literature:

With sodium hydroxide; In methanol; a) 0 deg C, 1 h, b) RT, 4 h;

DOI:10.1021/jm00142a002

Reference yield:

Boc-Tyr-OH (3978-80-1) → N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanine (71591-34-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-methylmorpholine, DCC, 1-hydroxybenzotriazole / 1.) 1 h, 0 deg C, 7 h, 20 deg C

2: 1 N aq. NaOH / methanol; dioxane / 0.33 h / 20 °C

With 4-methyl-morpholine; sodium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In 1,4-dioxane; methanol;

Reference yield:

D-Alanine (338-69-2,25191-17-7,18875-37-1) + Boc-Tyr-OH (3978-80-1) → N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanine (71591-34-9)

Guidance literature:

Boc-Tyr-OH; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

D-Alanine; With N,N,N',N'-tetramethylguanidine; In N,N-dimethyl-formamide;

DOI:10.1021/acsmedchemlett.6b00381

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanine methyl ester

Boc-Tyr-OH

Boc-(L)(α-Me)Tyr-OH

D-Alanine

Downstream raw materials:

N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanylglycine methyl ester

N-Boc-L-tyrosyl-D-alanyl-L-phenylalanyl-glycine

N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-methionine methyl ester

Boc-Tyr-D-Ala-Phe-gGly-D-COCH(CH₃)C₆H₅