(-)-(3aR,6aS)-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester

Base Information

• Chemical Name: (-)-(3aR,6aS)-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester
• CAS No.: 648936-11-2
• Molecular Formula: C₂₉H₃₇N₃O₆
• Molecular Weight: 523.629
• Mol file: 648936-11-2.mol

Synonyms:(-)-(3aR,6aS)-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester

Chemical Property of (-)-(3aR,6aS)-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3aR,6aS)-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester

There total 16 articles about (-)-(3aR,6aS)-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl 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: 90.0%

(3aS,6aR)-(3,3-dimethoxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone (648936-10-1) + Cbz-L-Leucine fluoride (134037-95-9) → (-)-(3aR,6aS)-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester (648936-11-2)

Guidance literature:

In DMF (N,N-dimethyl-formamide); for 1h;

Reference yield:

(R)-2-(2-aminoethyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester (648936-21-4) → (-)-(3aR,6aS)-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester (648936-11-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium carbonate / dioxane; H₂O / 1 h

2.1: meta-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 20 °C

3.1: hydrogen / Pd/C / ethanol / 0 - 20 °C

3.2: 61 percent / sodium carbonate / dioxane; H₂O / 1 h

4.1: HCl / dioxane / 1.08 h / 20 °C

5.1: N-methylmorpholine / dimethylformamide / 1.75 h / 20 °C

6.1: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 16 h

7.1: 77 percent / para-toluenesulfonic acid / methanol / 16 h / 65 °C

8.1: hydrogen / Pd/C / methanol / 1.42 h / 20 °C

9.1: 0.55 g / dimethylformamide / 1 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; hydrogen; sodium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Schotten-Baumann reaction / 3.2: Schotten-Baumann reaction;

DOI:10.1016/j.bmc.2004.10.060

Reference yield:

(S)-2-(2-diazoacetyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester (648930-83-0) → (-)-(3aR,6aS)-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester (648936-11-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 72 percent / silver trifluoroacetate; N-methylmorpholine / tetrahydrofuran / 6 h / 0 - 20 °C

2.1: 67 percent / lithium borohydride / methanol; tetrahydrofuran / 1.25 h

3.1: 3.42 g / triethylamine / CH₂Cl₂ / 1 h / 0 °C

4.1: sodium azide / dimethylformamide / 1.5 h / 60 °C

5.1: triphenylphosphine / tetrahydrofuran / 7.5 h / 45 °C

6.1: sodium carbonate / dioxane; H₂O / 1 h

7.1: meta-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 20 °C

8.1: hydrogen / Pd/C / ethanol / 0 - 20 °C

8.2: 61 percent / sodium carbonate / dioxane; H₂O / 1 h

9.1: HCl / dioxane / 1.08 h / 20 °C

10.1: N-methylmorpholine / dimethylformamide / 1.75 h / 20 °C

11.1: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 16 h

12.1: 77 percent / para-toluenesulfonic acid / methanol / 16 h / 65 °C

13.1: hydrogen / Pd/C / methanol / 1.42 h / 20 °C

14.1: 0.55 g / dimethylformamide / 1 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; lithium borohydride; sodium azide; hydrogen; silver trifluoroacetate; sodium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Wolff rearrangement / 6.1: Schotten-Baumann reaction / 8.2: Schotten-Baumann reaction;

DOI:10.1016/j.bmc.2004.10.060

upstream raw materials:

(3aS,6aR)-(3,3-dimethoxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone

Cbz-L-Leucine fluoride

(S)-2-(2-diazoacetyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

(R)-2-(2-aminoethyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(-)-(3aR,6aS)-N-[(1S)-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]-4-tert-butylbenzamide

(2S,3aR,6aS)-2-amino-1-(4-benzoyl-6,6-dimethoxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)-4-methylpentan-1-one