(S)-N-benzyloxycarbonyl-3-(4-tert-butyldimethylsilyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester

Base Information

Chemical Name:(S)-N-benzyloxycarbonyl-3-(4-tert-butyldimethylsilyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester
CAS No.:688360-31-8
Molecular Formula:C₃₀H₄₄BNO₇Si
Molecular Weight:569.578
Hs Code.:

Synonyms:(S)-N-benzyloxycarbonyl-3-(4-tert-butyldimethylsilyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester

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Chemical Property of (S)-N-benzyloxycarbonyl-3-(4-tert-butyldimethylsilyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester

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Technology Process of (S)-N-benzyloxycarbonyl-3-(4-tert-butyldimethylsilyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester

There total 5 articles about (S)-N-benzyloxycarbonyl-3-(4-tert-butyldimethylsilyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl)alanine 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: 66.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 688360-30-7
(S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester

: 688360-31-8
(S)-N-benzyloxycarbonyl-3-(4-tert-butyldimethylsilyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 17h;
DOI:10.1071/CH03181

Reference yield:

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

: 688360-31-8
(S)-N-benzyloxycarbonyl-3-(4-tert-butyldimethylsilyloxy-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: SOCl₂ / 18 h / 20 °C

2: 6.92 g / Na₂CO₃ / methanol; toluene / 2 h / 0 °C

3: 32 percent / Pd(dppf)Cl₂*CH₂Cl₂; KOAc / dimethylsulfoxide / 24 h / 80 °C

4: 66 percent / imidazole / dimethylformamide / 17 h / 20 °C

With 1H-imidazole; thionyl chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium carbonate; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1071/CH03181

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 688360-31-8
(S)-N-benzyloxycarbonyl-3-(4-tert-butyldimethylsilyloxy-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: 6.92 g / Na₂CO₃ / methanol; toluene / 2 h / 0 °C

2: 32 percent / Pd(dppf)Cl₂*CH₂Cl₂; KOAc / dimethylsulfoxide / 24 h / 80 °C

3: 66 percent / imidazole / dimethylformamide / 17 h / 20 °C

With 1H-imidazole; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium carbonate; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1071/CH03181