L-Tyrosine, N-[(phenylmethoxy)carbonyl]-O-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)-, phenylmethyl ester

Base Information

• Chemical Name: L-Tyrosine, N-[(phenylmethoxy)carbonyl]-O-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)-, phenylmethyl ester
• CAS No.: 600737-82-4
• Molecular Formula: C37H40BNO7
• Molecular Weight: 621.538
• Mol file: 600737-82-4.mol

Synonyms:

Chemical Property of L-Tyrosine, N-[(phenylmethoxy)carbonyl]-O-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)-, phenylmethyl ester

Chemical Property:

• PSA: 92.32000
• LogP: 6.53660

Purity/Quality:

O-Benzyl-N-[(benzyloxy)carbonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-tyrosineBenzylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: O-Benzyl-N-[(benzyloxy)carbonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-tyrosine Benzyl Ester is an intermediate in the preparation of L,L-Dityrosine Dihydrochloride (D494290).

Technology Process of L-Tyrosine, N-[(phenylmethoxy)carbonyl]-O-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)-, phenylmethyl ester

There total 9 articles about L-Tyrosine, N-[(phenylmethoxy)carbonyl]-O-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)-, phenylmethyl 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: 85.0%

bis(pinacol)diborane (73183-34-3) + benzyl (S)-3-(4-(benzyloxy)-3-iodophenyl)-2-(((benzyloxy)carbonyl)amino)propanoate (600737-79-9) → (S)-2-Benzyloxycarbonylamino-3-[4-benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester (600737-82-4)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 24h;

DOI:10.1016/S0040-4039(03)01081-5

Reference yield:

(S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-3-iodo-phenyl)-propionic acid benzyl ester (213757-66-5) → (S)-2-Benzyloxycarbonylamino-3-[4-benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester (600737-82-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 23 percent / Pd(dppf)Cl₂; Et₃N / dimethylsulfoxide

2: 80 percent / K₂CO₃; TBAI

3: 90 percent / I₂; Ag₂SO₄

4: 85 percent / KOAc; Pd(dppf)Cl₂ / dimethylsulfoxide / 24 h / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; iodine; potassium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; silver sulfate; triethylamine; In dimethyl sulfoxide; 4: Miyaura borylation;

DOI:10.1016/S0040-4039(03)01081-5

Reference yield:

3-Iodo-L-tyrosine (70-78-0) → (S)-2-Benzyloxycarbonylamino-3-[4-benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester (600737-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: aq. potassium carbonate / toluene / 21 h / 20 °C

2.1: K₂CO₃; tetrabutylammonium iodide / acetone / 0.25 h

2.2: 7.63 g / acetone / 20 h / Heating

3.1: 85 percent / KOAc; Pd(dppf)Cl₂*CH₂Cl₂ / dimethylsulfoxide / 24 h / 80 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; In dimethyl sulfoxide; acetone; toluene;

DOI:10.1021/jo051076m

upstream raw materials:

bis(pinacol)diborane

benzyl (S)-3-(4-(benzyloxy)-3-iodophenyl)-2-(((benzyloxy)carbonyl)amino)propanoate

3-Iodo-L-tyrosine

benzyl chloroformate

Downstream raw materials:

(S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl ester

(S)-2-Benzyloxycarbonylamino-3-[6,2'-bis-benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-biphenyl-3-yl]-propionic acid benzyl ester