(2S,3R)-2-[3-(4-Benzyloxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-methoxy-3-(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-Benzyloxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester
CAS No.:339221-03-3
Molecular Formula:C₄₅H₆₂BNO₉
Molecular Weight:771.8
Hs Code.:

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

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

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

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

There total 6 articles about (2S,3R)-2-[3-(4-Benzyloxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-methoxy-3-(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: 60.0%

: 339221-02-2
(2S,3R)-2-[3-(4-Benzyloxy-phenyl)-propyl]-3-[(S)-2-(3-iodo-4-methoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-5-methyl-hexanoic acid tert-butyl ester

: 73183-34-3
bis(pinacol)diborane

: 339221-03-3
(2S,3R)-2-[3-(4-Benzyloxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester

Guidance literature:: With potassium acetate; PdCl₂(pddf); In N,N-dimethyl-formamide; at 80 ℃; for 18h;
DOI:10.1021/ol015572i

Reference yield:

: 70277-02-0
3-iodo-L-tyrosine methyl ester

: 339221-03-3
(2S,3R)-2-[3-(4-Benzyloxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / TBTU; NMM / dimethylformamide / 6 h / 0 - 20 °C

2: 89 percent / hexane; methanol / 2.5 h / 20 °C

3: 60 percent / potassium acetate / PdCl₂(pddf) / dimethylformamide / 18 h / 80 °C

With 4-methyl-morpholine; potassium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; PdCl₂(pddf); In methanol; hexane; N,N-dimethyl-formamide;
DOI:10.1021/ol015572i

Reference yield:

: 112245-04-2
(R)-2-(2-(tert-butoxy)-2-oxoethyl)-4-methylpentanoic acid

: 339221-03-3
(2S,3R)-2-[3-(4-Benzyloxy-phenyl)-propyl]-3-{(S)-1-methoxycarbonyl-2-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylcarbamoyl}-5-methyl-hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: LDA

2: 72 percent / TBTU; NMM / dimethylformamide / 6 h / 0 - 20 °C

3: 89 percent / hexane; methanol / 2.5 h / 20 °C

4: 60 percent / potassium acetate / PdCl₂(pddf) / dimethylformamide / 18 h / 80 °C

With 4-methyl-morpholine; potassium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; lithium diisopropyl amide; PdCl₂(pddf); In methanol; hexane; N,N-dimethyl-formamide;
DOI:10.1021/ol015572i