(3S,6S,9S)-6-azido-6-benzyl-5-oxooctahydroindolizine-3-carboxylic acid 4-N-Cbz-carbamimidoylbenzylamide

Base Information

Chemical Name:(3S,6S,9S)-6-azido-6-benzyl-5-oxooctahydroindolizine-3-carboxylic acid 4-N-Cbz-carbamimidoylbenzylamide
CAS No.:612820-35-6
Molecular Formula:C₃₂H₃₃N₇O₄
Molecular Weight:579.659
Hs Code.:

Synonyms:(3S,6S,9S)-6-azido-6-benzyl-5-oxooctahydroindolizine-3-carboxylic acid 4-N-Cbz-carbamimidoylbenzylamide

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Chemical Property of (3S,6S,9S)-6-azido-6-benzyl-5-oxooctahydroindolizine-3-carboxylic acid 4-N-Cbz-carbamimidoylbenzylamide

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Technology Process of (3S,6S,9S)-6-azido-6-benzyl-5-oxooctahydroindolizine-3-carboxylic acid 4-N-Cbz-carbamimidoylbenzylamide

There total 20 articles about (3S,6S,9S)-6-azido-6-benzyl-5-oxooctahydroindolizine-3-carboxylic acid 4-N-Cbz-carbamimidoylbenzylamide 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:

: 161424-44-8
<2S-trans-(Z)>-5-Propenyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl diester

: 612820-35-6
(3S,6S,9S)-6-azido-6-benzyl-5-oxooctahydroindolizine-3-carboxylic acid 4-N-Cbz-carbamimidoylbenzylamide

Guidance literature:: Multi-step reaction with 13 steps

1.1: trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

2.1: 3.39 g / EDC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.75 h

3.1: 96 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 4 h / Heating

4.1: 94 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 2 h

5.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

6.1: sodium borohydride / methanol / 2 h / 20 °C

7.1: 772 mg / imidazole / dimethylformamide / 16 h / 20 °C

8.1: 96 percent / hydrogen / Pd/C / ethyl acetate / 16 h / 20 °C

9.1: t-BuLi / tetrahydrofuran; pentane / 0.75 h / -78 °C

9.2: 67 percent / tetrahydrofuran; pentane / 1 h / -78 °C

10.1: t-BuLi / tetrahydrofuran; pentane / 0.83 h / -78 °C

10.2: 27 percent / trisyl azide / tetrahydrofuran; pentane / 6 h / -78 °C

11.1: 99 percent / TBAF / tetrahydrofuran / 1.5 h

12.1: pyridinium dichromate / dimethylformamide; H₂O

13.1: 104 mg / EDC; HOBt; i-Pr₂NEt / dimethylformamide

With 1H-imidazole; dmap; lithium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; Grubbs catalyst first generation; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; pentane; 3.1: Grubbs olefin metathesis reaction;

Reference yield:

: (2S,5S)-((Z)-5-Propenyl)-pyrrolidine-2-carboxylic acid methyl ester

: 612820-35-6
(3S,6S,9S)-6-azido-6-benzyl-5-oxooctahydroindolizine-3-carboxylic acid 4-N-Cbz-carbamimidoylbenzylamide

Guidance literature:: Multi-step reaction with 12 steps

1.1: 3.39 g / EDC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.75 h

2.1: 96 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 4 h / Heating

3.1: 94 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 2 h

4.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

5.1: sodium borohydride / methanol / 2 h / 20 °C

6.1: 772 mg / imidazole / dimethylformamide / 16 h / 20 °C

7.1: 96 percent / hydrogen / Pd/C / ethyl acetate / 16 h / 20 °C

8.1: t-BuLi / tetrahydrofuran; pentane / 0.75 h / -78 °C

8.2: 67 percent / tetrahydrofuran; pentane / 1 h / -78 °C

9.1: t-BuLi / tetrahydrofuran; pentane / 0.83 h / -78 °C

9.2: 27 percent / trisyl azide / tetrahydrofuran; pentane / 6 h / -78 °C

10.1: 99 percent / TBAF / tetrahydrofuran / 1.5 h

11.1: pyridinium dichromate / dimethylformamide; H₂O

12.1: 104 mg / EDC; HOBt; i-Pr₂NEt / dimethylformamide

With 1H-imidazole; dmap; lithium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; Grubbs catalyst first generation; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; pentane; 2.1: Grubbs olefin metathesis reaction;

Reference yield:

: (3S,8aS)-3-Hydroxymethyl-2,3,6,8a-tetrahydro-1H-indolizin-5-one

: 612820-35-6
(3S,6S,9S)-6-azido-6-benzyl-5-oxooctahydroindolizine-3-carboxylic acid 4-N-Cbz-carbamimidoylbenzylamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 772 mg / imidazole / dimethylformamide / 16 h / 20 °C

2.1: 96 percent / hydrogen / Pd/C / ethyl acetate / 16 h / 20 °C

3.1: t-BuLi / tetrahydrofuran; pentane / 0.75 h / -78 °C

3.2: 67 percent / tetrahydrofuran; pentane / 1 h / -78 °C

4.1: t-BuLi / tetrahydrofuran; pentane / 0.83 h / -78 °C

4.2: 27 percent / trisyl azide / tetrahydrofuran; pentane / 6 h / -78 °C

5.1: 99 percent / TBAF / tetrahydrofuran / 1.5 h

6.1: pyridinium dichromate / dimethylformamide; H₂O

7.1: 104 mg / EDC; HOBt; i-Pr₂NEt / dimethylformamide

With 1H-imidazole; dipyridinium dichromate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; pentane;