L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester, hydrogen sulfate (ester), monosodium salt

Base Information

• Chemical Name: L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester, hydrogen sulfate (ester), monosodium salt
• CAS No.: 110071-96-0
• Molecular Formula: C15H21NO8S.Na
• Molecular Weight: 397.381
• Mol file: 110071-96-0.mol

Synonyms:

Chemical Property of L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester, hydrogen sulfate (ester), monosodium salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester, hydrogen sulfate (ester), monosodium salt

There total 2 articles about L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester, hydrogen sulfate (ester), monosodium salt 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: 87.0%

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) → sodium salt of tert-butyloxycarbonyl-O-sulfotyrosine α-methyl ester (110071-96-0)

Guidance literature:

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester; With methyl chlorosulfate; In N,N-dimethyl-formamide; at -20 - 5 ℃; for 1.25h;

DOI:10.1002/chem.202100527

Reference yield:

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)-oxy)phenyl)propanoate (112196-57-3) → sodium salt of tert-butyloxycarbonyl-O-sulfotyrosine α-methyl ester (110071-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / 80 °C / Inert atmosphere

2: 20% palladium hydroxide-activated charcoal; hydrogen / methanol; acetonitrile; aq. phosphate buffer / 2 h / 20 °C

With 20% palladium hydroxide-activated charcoal; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; aq. phosphate buffer; acetonitrile;

DOI:10.1002/anie.202007211

Reference yield: 43.0%

sodium salt of tert-butyloxycarbonyl-O-sulfotyrosine α-methyl ester (110071-96-0) + H-Nle-Gly-Trp-Aib-Asp-Phe-NH2 → Sodium; (S)-3-{2-[(S)-2-(2-{(S)-2-[(S)-2-tert-butoxycarbonylamino-3-(4-sulfooxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-(1H-indol-3-yl)-propionylamino]-2-methyl-propionylamino}-3-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-propionate (130832-21-2)

Guidance literature:

With sodium hydroxide; ethylenediaminetetraacetic acid; carbonate-bicarbonate buffer; diothiothreitol; In methanol; at 30 ℃; for 0.5h; pH 9.1, aq. papain;

upstream raw materials:

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)-oxy)phenyl)propanoate

Downstream raw materials:

Sodium; (S)-3-{2-[(S)-2-(2-{(S)-2-[(S)-2-tert-butoxycarbonylamino-3-(4-sulfooxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-(1H-indol-3-yl)-propionylamino]-2-methyl-propionylamino}-3-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-propionate