(2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

Base Information

Chemical Name:(2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester
CAS No.:187872-17-9
Molecular Formula:C₃₉H₄₄N₂O₆
Molecular Weight:636.788
Hs Code.:

(2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

Synonyms:(2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

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Chemical Property of (2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

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Technology Process of (2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

There total 10 articles about (2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic 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: 98.0%

: 136918-14-4,85-41-6
phthalimide

: (2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-hydroxymethyl-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

: 187872-17-9
(2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 16h;
DOI:10.1021/jm960553d

Reference yield:

: 16874-08-1
L-Isoleucin-tert-butylester

: 187872-17-9
(2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / tetrahydrofuran / 120 h / 80 °C

2: 1M aq. NaOH / dioxane / 6 h / Ambient temperature

3: DPPA, Na₂CO₃ / dimethylformamide / 72 h / 0 °C

4: 71 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran; CH₂Cl₂ / 6 h / Ambient temperature

5: 1.) LDA / 1.) THF, -40 deg C, 20 min, 2.) THF, a) -78 deg C, 10 min, b) -25 deg C, 30 min

6: 98 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 16 h

With sodium hydroxide; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; sodium carbonate; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm960553d

Reference yield:

: 69320-89-4
L-isoleucine tert-butyl ester hydrochloride

: 187872-17-9
(2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: NaOAc, NaBH₃CN, 3A molecular sieves / methanol / 2 h / Ambient temperature

2: 1M aq. NaOH / dioxane / 6 h / Ambient temperature

3: DPPA, Na₂CO₃ / dimethylformamide / 72 h / 0 °C

4: 71 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran; CH₂Cl₂ / 6 h / Ambient temperature

5: 1.) LDA / 1.) THF, -40 deg C, 20 min, 2.) THF, a) -78 deg C, 10 min, b) -25 deg C, 30 min

6: 98 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 16 h

With sodium hydroxide; 3 A molecular sieve; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; sodium acetate; sodium cyanoborohydride; sodium carbonate; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm960553d