N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester

Base Information

• Chemical Name: N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester
• CAS No.: 127103-00-8
• Molecular Formula: C₃₁H₃₂NO₁₀P
• Molecular Weight: 609.57
• Mol file: 127103-00-8.mol

Synonyms:N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester

Chemical Property of N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester

There total 3 articles about N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl 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:

2-(bromomethyl)anthraquinone (7598-10-9) → Nα-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester (127103-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 1.5 h / Heating

2: 1) 1H-tetrazole, 2) 85percent m-chloroperoxybenzoic acid / 1) THF, 20 deg C, 20 min, 2) 20 deg C, 10 min

With 1H-tetrazole; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran;

DOI:10.1021/jo00300a041

Reference yield:

Boc-Tyr-OH (3978-80-1) → Nα-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester (127103-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 1.5 h / Heating

2: 1) 1H-tetrazole, 2) 85percent m-chloroperoxybenzoic acid / 1) THF, 20 deg C, 20 min, 2) 20 deg C, 10 min

With 1H-tetrazole; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran;

DOI:10.1021/jo00300a041

Reference yield:

dimethoxy(diethylamino)phosphine (20621-25-4) + Nα-(tert-butoxycarbonyl)tyrosine anthraquinon-2-ylmethylester (119255-37-7) → Nα-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester (127103-00-8)

Guidance literature:

With 1H-tetrazole; 3-chloro-benzenecarboperoxoic acid; Yield given. Multistep reaction; 1) THF, 20 deg C, 20 min, 2) 20 deg C, 10 min;

DOI:10.1021/jo00300a041

upstream raw materials:

dimethoxy(diethylamino)phosphine

N^α-(tert-butoxycarbonyl)tyrosine anthraquinon-2-ylmethylester

2-(bromomethyl)anthraquinone

Boc-Tyr-OH

Downstream raw materials:

TFA*H-Tyr(PO₃Me₂)-Val-OMaq

N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosylvaline anthraquinon-2-ylmethyl ester

N^α-(tert-butoxycarbonyl)-O-(O',O''-dimethylphosphoro)-L-tyrosine