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

Base Information

Chemical Name:N-[(1,1-Dimethylethoxy)carbonyl]-O-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-tyrosine
CAS No.:612484-56-7
Molecular Formula:C₂₁H₃₂BNO₇
Molecular Weight:421.299
Hs Code.:
DSSTox Substance ID:DTXSID601113416

Synonyms:DTXSID601113416;612484-56-7;N-[(1,1-Dimethylethoxy)carbonyl]-O-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-tyrosine

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

Supply Marketing:

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

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

Chemical Property:

Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:8
Exact Mass:421.2271825
Heavy Atom Count:30
Complexity:615

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

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

There total 8 articles about N-[(1,1-Dimethylethoxy)carbonyl]-O-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-tyrosine 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: 100.0%

: 675832-36-7
(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxy-3-(4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)phenyl)propanoate

: 612484-56-7
(S)-2-(tert-butoxycarbonylamino)-3-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃;
DOI:10.1002/anie.200351996

Reference yield: 99.0%

: 113850-71-8
(S )-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-iodo-4-methoxyphenyl)propanoate

: 73183-34-3
bis(pinacol)diborane

: 612484-56-7
(S)-2-(tert-butoxycarbonylamino)-3-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid

Guidance literature:: With lithium hydroxide; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; dimethyl sulfoxide; a) B-comp., Pd-comp., tyrosine-comp., CH3COOK, DMSO, 80%; b)LiOH, THF/H2O 1:1, room temp.;
DOI:10.1002/anie.200351996

Reference yield:

: 113850-71-8
(S )-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-iodo-4-methoxyphenyl)propanoate

: 612484-56-7
(S)-2-(tert-butoxycarbonylamino)-3-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / [PdCl₂(1,1'-bis(diphenylphosphano)ferrocene)]; KOAc / dimethylsulfoxide

2: 100 percent / LiOH / tetrahydrofuran; H₂O / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; potassium acetate; In tetrahydrofuran; water; dimethyl sulfoxide;
DOI:10.1002/anie.200351996