(4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

Base Information

Chemical Name:(4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester
CAS No.:392724-90-2
Molecular Formula:C₃₂H₅₆N₂O₆Si
Molecular Weight:592.892
Hs Code.:

Synonyms:(4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

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Chemical Property of (4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of (4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

There total 8 articles about (4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl 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: 81.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 392725-01-8
(4R,5R)-4-((S)-3-Benzyloxy-2-methyl-propylamino)-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 392724-90-2
(4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/ol016799g

Reference yield:

: (1S,7R)-8-Oxa-4-aza-bicyclo[5.1.0]octane-4-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 392724-90-2
(4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: azidotrimethylsilane / (S,S)-Jacobsen Cr(salen) catalyst / diethyl ether / 144 h

1.2: 1S-(+)-10-camphorsulfuric acid / methanol / 0.5 h

2.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

2.2: 88 percent / tetramethylammonium iodide / tetrahydrofuran / 0.5 h / 20 °C

3.1: 98 percent / H₂ / Pd/C / methanol / 12 h / 20 °C

4.1: 73 percent / NaBH₃CN; molecular sieves 4 Angstroem / methanol; acetic acid / 1 h / 20 °C / pH 6 - 7

5.1: 81 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

With trimethylsilylazide; 4 A molecular sieve; hydrogen; sodium hydride; sodium cyanoborohydride; triethylamine; palladium on activated charcoal; (S,S)-Jacobsen Cr(salen) catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid;
DOI:10.1021/ol016799g

Reference yield:

: 132365-02-7
N-benzyl-N-(but-3-enyl)-but-3-en-1-amine

: 392724-90-2
(4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 58 percent / tetrahydrofuran / 12 h / 20 °C

2.1: 90 percent / (benzylidene)Ru(PCy₃)2Cl₂ / CH₂Cl₂ / 24 h / Heating

3.1: 83 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 12 h / 0 °C

4.1: azidotrimethylsilane / (S,S)-Jacobsen Cr(salen) catalyst / diethyl ether / 144 h

4.2: 1S-(+)-10-camphorsulfuric acid / methanol / 0.5 h

5.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

5.2: 88 percent / tetramethylammonium iodide / tetrahydrofuran / 0.5 h / 20 °C

6.1: 98 percent / H₂ / Pd/C / methanol / 12 h / 20 °C

7.1: 73 percent / NaBH₃CN; molecular sieves 4 Angstroem / methanol; acetic acid / 1 h / 20 °C / pH 6 - 7

8.1: 81 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

With trimethylsilylazide; 4 A molecular sieve; hydrogen; sodium hydride; sodium cyanoborohydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; Grubbs catalyst first generation; (S,S)-Jacobsen Cr(salen) catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid;
DOI:10.1021/ol016799g