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

Base Information

Chemical Name:O-Methyl-N-[(phenylmethoxy)carbonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-tyrosine methyl ester
CAS No.:353520-75-9
Molecular Formula:C₂₅H₃₂BNO₇
Molecular Weight:469.343
Hs Code.:
DSSTox Substance ID:DTXSID801109114
Nikkaji Number:J1.545.270F

Synonyms:DTXSID801109114;353520-75-9;O-Methyl-N-[(phenylmethoxy)carbonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-tyrosine methyl ester

Suppliers and Price of O-Methyl-N-[(phenylmethoxy)carbonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-tyrosine methyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:10
Exact Mass:469.2271825
Heavy Atom Count:34
Complexity:679

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:B1(OC(C(O1)(C)C)(C)C)C2=C(C=CC(=C2)CC(C(=O)OC)NC(=O)OCC3=CC=CC=C3)OC
Isomeric SMILES:B1(OC(C(O1)(C)C)(C)C)C2=C(C=CC(=C2)C[C@@H](C(=O)OC)NC(=O)OCC3=CC=CC=C3)OC

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

There total 9 articles about O-Methyl-N-[(phenylmethoxy)carbonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-tyrosine methyl 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: 95.0%

: 73183-34-3
bis(pinacol)diborane

: 353520-84-0
(S)-N-benzyloxycarbonyl-3-(3-iodo-4-methoxyphenyl)alanine methyl ester

: 353520-75-9
(S)-N-benzyloxycarbonyl-3-(4-methoxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 13h;
DOI:10.1002/1521-3773(20010518)40:10<1967::AID-ANIE1967>3.0.CO;2-Q

Reference yield:

: 13512-31-7
N-(benzyloxycarbonyl)-L-tyrosine methyl ester

: 353520-75-9
(S)-N-benzyloxycarbonyl-3-(4-methoxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / LiOH

2: 93 percent / I₂; Ag₂SO₄ / methanol / 1.5 h / 20 °C

3: 95 percent / [PdCl₂(dppf)]*CH₂Cl₂; KOAc / dimethylsulfoxide / 13 h / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; iodine; potassium acetate; silver sulfate; In methanol; dimethyl sulfoxide; 3: Miyaura reaction;
DOI:10.1021/ja049821k

Reference yield:

: 1080-06-4
L-Tyr-OMe

: 353520-75-9
(S)-N-benzyloxycarbonyl-3-(4-methoxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / Na₂CO₃ / acetone; H₂O / 2 h / 20 °C

2: 86 percent / LiOH

3: 93 percent / I₂; Ag₂SO₄ / methanol / 1.5 h / 20 °C

4: 95 percent / [PdCl₂(dppf)]*CH₂Cl₂; KOAc / dimethylsulfoxide / 13 h / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; iodine; potassium acetate; sodium carbonate; silver sulfate; In methanol; water; dimethyl sulfoxide; acetone; 4: Miyaura reaction;
DOI:10.1021/ja049821k