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

Base Information

• Chemical Name: N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosylvaline anthraquinon-2-ylmethyl ester
• CAS No.: 118903-64-3
• Molecular Formula: C₃₆H₄₁N₂O₁₁P
• Molecular Weight: 708.702

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosylvaline 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:

Boc-Tyr-OH (3978-80-1) → Nα-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosylvaline anthraquinon-2-ylmethyl ester (118903-64-3)

Guidance literature:

Multi-step reaction with 4 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

3: 75 percent / sodium dithionite, sodium carbonate / acetonitrile; H₂O / 1 h / 50 °C

4: 1) N-methylmorpholine, isobutyl chloroformate, 2) N-methylmorpholine / 1) THF, -15 deg C, 3 min, 2) THF, -20 deg C, 2 h

With 4-methyl-morpholine; 1H-tetrazole; sodium dithionite; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; isobutyl chloroformate; In tetrahydrofuran; water; acetonitrile;

DOI:10.1021/jo00300a041

Reference yield:

Nα-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester (127103-00-8) → Nα-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosylvaline anthraquinon-2-ylmethyl ester (118903-64-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / sodium dithionite, sodium carbonate / acetonitrile; H₂O / 1 h / 50 °C

2: 1) N-methylmorpholine, isobutyl chloroformate, 2) N-methylmorpholine / 1) THF, -15 deg C, 3 min, 2) THF, -20 deg C, 2 h

With 4-methyl-morpholine; sodium dithionite; sodium carbonate; isobutyl chloroformate; In water; acetonitrile;

DOI:10.1021/jo00300a041

Reference yield:

Nα-(tert-butoxycarbonyl)tyrosine anthraquinon-2-ylmethylester (119255-37-7) → Nα-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosylvaline anthraquinon-2-ylmethyl ester (118903-64-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 75 percent / sodium dithionite, sodium carbonate / acetonitrile; H₂O / 1 h / 50 °C

3: 1) N-methylmorpholine, isobutyl chloroformate, 2) N-methylmorpholine / 1) THF, -15 deg C, 3 min, 2) THF, -20 deg C, 2 h

With 4-methyl-morpholine; 1H-tetrazole; sodium dithionite; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; isobutyl chloroformate; In water; acetonitrile;

DOI:10.1021/jo00300a041

upstream raw materials:

Boc-Tyr-OH

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

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

Downstream raw materials:

TFA*H-Tyr(PO₃Me₂)-Val-OMaq

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