N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

Base Information

Chemical Name:N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester
CAS No.:143145-69-1
Molecular Formula:C₄₂H₄₇N₃O₁₃
Molecular Weight:801.847
Hs Code.:

N-<N-<(phenylmethoxy)carbonyl>-D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

Synonyms:N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

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Chemical Property of N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

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Technology Process of N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

There total 22 articles about N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl 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: 90.0%

: 143171-01-1
N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>amino<<<(trimethylsilyl)ethyl>oxy>carbonyl>methyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

: 143145-69-1
N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h; Ambient temperature;
DOI:10.1021/jo00046a031

Reference yield:

: 2150-44-9
1-carbomethoxy-3,5-dihydroxybenzene

: 143145-69-1
N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

Guidance literature:: Multi-step reaction with 19 steps

1: 65 percent / K₂CO₃, Bu₄NI / acetone / 3 h / Heating

2: 1) NaH / 1) DMF, r.t., 0.5 h, 2) 90 deg C, 3 h

3: 95 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 1) DIBALH, 2) 1N HCl / 1) a) CH₂Cl₂, -78 deg C, 0.5 h, 2) MeOH, 0 deg C, 0.5 h

5: 86 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 0 °C

6: CHCl₃ / 5 h / Ambient temperature

7: methanol / 3 h

8: 90 percent / ethereal HCl / 5 h / Ambient temperature

9: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / 0 °C / 1) CH₂Cl₂, MeOH, 0 deg C, 5 min, 2) phosphate buffer pH 7, r.t., 0.5 h

10: 3N HCl / diethyl ether / 0.25 h / Ambient temperature

11: 1) 1-hydroxybenzotriazole hydrate, 1,3-dicyclohexylcarbodiimide / 1) DMF, 0 deg C, 30 min, 2) DMF, 0 deg C to r.t., 1,5 h

12: 85 percent / mercuric oxide, mercuric chloride / acetonitrile; H₂O / 2 h / Ambient temperature

13: CHCl₃ / 24 h / Ambient temperature

14: CHCl₃ / 24 h / Ambient temperature

15: 52 percent / ethereal HCl / CHCl₃ / 3 h / Ambient temperature

16: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / ice-cold

17: 3N HCl / diethyl ether / 0.25 h / Ambient temperature

18: 80 percent / CH₂Cl₂ / 3 h / Ambient temperature

19: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With lead(IV) acetate; hydrogenchloride; methanol; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; pyridinium chlorochromate; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; acetone; acetonitrile;
DOI:10.1021/jo00046a031

Reference yield:

: 19520-74-2
3-hydroxy-5-methoxy-benzoic acid methyl ester

: 143145-69-1
N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 1) NaH / 1) DMF, r.t., 0.5 h, 2) 90 deg C, 3 h

2: 95 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 1) DIBALH, 2) 1N HCl / 1) a) CH₂Cl₂, -78 deg C, 0.5 h, 2) MeOH, 0 deg C, 0.5 h

4: 86 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 0 °C

5: CHCl₃ / 5 h / Ambient temperature

6: methanol / 3 h

7: 90 percent / ethereal HCl / 5 h / Ambient temperature

8: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / 0 °C / 1) CH₂Cl₂, MeOH, 0 deg C, 5 min, 2) phosphate buffer pH 7, r.t., 0.5 h

9: 3N HCl / diethyl ether / 0.25 h / Ambient temperature

10: 1) 1-hydroxybenzotriazole hydrate, 1,3-dicyclohexylcarbodiimide / 1) DMF, 0 deg C, 30 min, 2) DMF, 0 deg C to r.t., 1,5 h

11: 85 percent / mercuric oxide, mercuric chloride / acetonitrile; H₂O / 2 h / Ambient temperature

12: CHCl₃ / 24 h / Ambient temperature

13: CHCl₃ / 24 h / Ambient temperature

14: 52 percent / ethereal HCl / CHCl₃ / 3 h / Ambient temperature

15: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / ice-cold

16: 3N HCl / diethyl ether / 0.25 h / Ambient temperature

17: 80 percent / CH₂Cl₂ / 3 h / Ambient temperature

18: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With lead(IV) acetate; hydrogenchloride; methanol; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; pyridinium chlorochromate; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; acetonitrile;
DOI:10.1021/jo00046a031