(S)-O-benzyl-N-tert-butoxycarbonyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tyrosine methyl ester

Base Information

Chemical Name:(S)-O-benzyl-N-tert-butoxycarbonyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tyrosine methyl ester
CAS No.:1338925-50-0
Molecular Formula:C₂₈H₃₈BNO₇
Molecular Weight:511.423
Hs Code.:

Synonyms:(S)-O-benzyl-N-tert-butoxycarbonyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tyrosine methyl ester

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Chemical Property of (S)-O-benzyl-N-tert-butoxycarbonyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tyrosine methyl ester

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Technology Process of (S)-O-benzyl-N-tert-butoxycarbonyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tyrosine methyl ester

There total 7 articles about (S)-O-benzyl-N-tert-butoxycarbonyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)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: 90.0%

: 73183-34-3
bis(pinacol)diborane

: 691394-91-9
methyl (S)-3-(4-(benzyloxy)-3-iodophenyl)-2-((tert-butoxycarbonyl)amino)propanoate

: 1338925-50-0
(S)-O-benzyl-N-tert-butoxycarbonyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tyrosine methyl ester

Guidance literature:: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 90 ℃; for 24h; Inert atmosphere;
DOI:10.1021/ja207318n

Reference yield:

: 119336-08-2,79677-59-1
methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate

: 1338925-50-0
(S)-O-benzyl-N-tert-butoxycarbonyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tyrosine methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: potassium carbonate / acetone / 4 h / Reflux

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 24 h / 90 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; potassium carbonate; In dimethyl sulfoxide; acetone; 2: Mukaiyama reaction;
DOI:10.1021/ja207318n

Reference yield:

: 70-78-0
3-Iodo-L-tyrosine

: 1338925-50-0
(S)-O-benzyl-N-tert-butoxycarbonyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tyrosine methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: thionyl chloride / 2 h / 0 °C / Reflux

2: sodium hydrogencarbonate / water; acetone

3: potassium carbonate / acetone / 4 h / Reflux

4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 24 h / 90 °C / Inert atmosphere

With thionyl chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium hydrogencarbonate; potassium carbonate; In water; dimethyl sulfoxide; acetone; 4: Mukaiyama reaction;
DOI:10.1021/ja207318n