(6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene

Base Information

Chemical Name:(6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene
CAS No.:173395-76-1
Molecular Formula:C₃₃H₄₅N₃O₅Si
Molecular Weight:591.823
Hs Code.:

(6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<<N-(carbobenzyloxy)-L-alanyl>amino>-2-oxobicyclo<4.3.0>non-3-ene

Synonyms:(6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene

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Chemical Property of (6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene

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Technology Process of (6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene

There total 9 articles about (6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene 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:

: (2S)-2-<(benzyloxy)methyl>-5-methoxy-1-(3-phenyl-4-pentenoyl)pyrrolidine

: 173395-76-1
(6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / TiCl₄ / CH₂Cl₂ / Ambient temperature

2: 78 percent / H₂, NaOMe / 5percent Pd/C / methanol

3: 90 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

4: 63 percent / n-BuLi, diisopropylamine, O₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

5: 45 percent / NH₃ / methanol / 1.) 0 deg C, 2.) room temperature, 3 d

6: 67 percent / HOBt, EDCI / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) room temperature, overnight

With n-butyllithium; ammonia; hydrogen; oxygen; sodium methylate; titanium tetrachloride; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/jo00130a015

Reference yield:

: (9S)-1-aza-4-(chlorobenzyl)-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>nonane

: 173395-76-1
(6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / H₂, NaOMe / 5percent Pd/C / methanol

2: 90 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

3: 63 percent / n-BuLi, diisopropylamine, O₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

4: 45 percent / NH₃ / methanol / 1.) 0 deg C, 2.) room temperature, 3 d

5: 67 percent / HOBt, EDCI / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) room temperature, overnight

With n-butyllithium; ammonia; hydrogen; oxygen; sodium methylate; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/jo00130a015

Reference yield:

: (2S)-2-(hydroxymethyl)-1-(3-phenyl-4-pentenoyl)pyrrolidine

: 173395-76-1
(6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene

Guidance literature:: Multi-step reaction with 8 steps

1: 87 percent / NaH / tetrahydrofuran; paraffin / Ambient temperature

2: 60 percent / Et₄NOTs / carbon anode, Pt cathode, 26.8 mA, 2.5 F/mol

3: 90 percent / TiCl₄ / CH₂Cl₂ / Ambient temperature

4: 78 percent / H₂, NaOMe / 5percent Pd/C / methanol

5: 90 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

6: 63 percent / n-BuLi, diisopropylamine, O₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

7: 45 percent / NH₃ / methanol / 1.) 0 deg C, 2.) room temperature, 3 d

8: 67 percent / HOBt, EDCI / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) room temperature, overnight

With n-butyllithium; ammonia; hydrogen; oxygen; sodium methylate; titanium tetrachloride; sodium hydride; tetraethylammonium tosylate; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; paraffin;
DOI:10.1021/jo00130a015