(2S,3R)-2-[3-(4-Hydroxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3R)-2-[3-(4-Hydroxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester
• CAS No.: 339220-98-3
• Molecular Formula: C₃₇H₅₄BNO₈
• Molecular Weight: 651.649
• Mol file: 339220-98-3.mol

Synonyms:(2S,3R)-2-[3-(4-Hydroxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester

Chemical Property of (2S,3R)-2-[3-(4-Hydroxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-[3-(4-Hydroxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester

There total 7 articles about (2S,3R)-2-[3-(4-Hydroxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl 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: 96.0%

(2S,3R)-2-[3-(4-Benzyloxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester (339220-97-2) → (2S,3R)-2-[3-(4-Hydroxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester (339220-98-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; at 25 ℃; for 16h; under 760.051 Torr;

DOI:10.1021/ol015572i

Reference yield:

(S)-methyl 2-amino-3-(4-iodophenyl)propanoate (113850-77-4) → (2S,3R)-2-[3-(4-Hydroxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester (339220-98-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / TBTU; NMM / dimethylformamide / 6 h / 0 - 20 °C

2: 93 percent / potassium acetate / PdCl₂(pddf) / dimethylformamide / 18 h / 80 °C

3: 96 percent / H₂ / Pd-C / methanol; ethyl acetate / 16 h / 25 °C / 760.05 Torr

With 4-methyl-morpholine; hydrogen; potassium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; palladium on activated charcoal; PdCl₂(pddf); In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol015572i

Reference yield:

(R)-2-(2-(tert-butoxy)-2-oxoethyl)-4-methylpentanoic acid (112245-04-2) → (2S,3R)-2-[3-(4-Hydroxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester (339220-98-3)

Guidance literature:

Multi-step reaction with 4 steps

1: LDA

2: 70 percent / TBTU; NMM / dimethylformamide / 6 h / 0 - 20 °C

3: 93 percent / potassium acetate / PdCl₂(pddf) / dimethylformamide / 18 h / 80 °C

4: 96 percent / H₂ / Pd-C / methanol; ethyl acetate / 16 h / 25 °C / 760.05 Torr

With 4-methyl-morpholine; hydrogen; potassium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; lithium diisopropyl amide; palladium on activated charcoal; PdCl₂(pddf); In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol015572i

upstream raw materials:

(2S,3R)-2-[3-(4-Benzyloxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester

(S)-methyl 2-amino-3-(4-iodophenyl)propanoate

(R)-2-(2-(tert-butoxy)-2-oxoethyl)-4-methylpentanoic acid

bis(pinacol)diborane

Downstream raw materials:

C₃₁H₄₄BNO₈