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

Base Information

Chemical Name:(-)-(3aR,6aS)-[(1S)-1-((6S)-4-benzoyl-6-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester
CAS No.:648936-16-7
Molecular Formula:C₂₇H₃₃N₃O₅
Molecular Weight:479.576
Hs Code.:

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

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

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

There total 16 articles about (-)-(3aR,6aS)-[(1S)-1-((6S)-4-benzoyl-6-hydroxyhexahydropyrrolo[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: 68.0%

: 648936-15-6
(3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone

: 134037-95-9
Cbz-L-Leucine fluoride

: 648936-16-7
(-)-(3aR,6aS)-[(1S)-1-((6S)-4-benzoyl-6-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester

Guidance literature:: In N,N-dimethyl-formamide; at 20 ℃; for 1.25h;
DOI:10.1016/j.bmc.2004.10.060

Reference yield: 60.0%

: 648936-15-6
(3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone

: Cbz-Leu-OSuc

: 648936-16-7
(-)-(3aR,6aS)-[(1S)-1-((6S)-4-benzoyl-6-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester

Guidance literature:: In DMF (N,N-dimethyl-formamide); for 20h;

Reference yield:

: 648930-84-1
(-)-(R)-2-(2-hydroxyethyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

: 648936-16-7
(-)-(3aR,6aS)-[(1S)-1-((6S)-4-benzoyl-6-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1-carbonyl)-3-methylbutyl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 3.42 g / triethylamine / CH₂Cl₂ / 1 h / 0 °C

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

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

4.1: sodium carbonate / dioxane; H₂O / 1 h

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

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

6.2: 61 percent / sodium carbonate / dioxane; H₂O / 1 h

7.1: HCl / dioxane / 1.08 h / 20 °C

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

9.1: hydrogen / Pd/C / ethanol

10.1: 68 percent / dimethylformamide / 1.25 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; sodium azide; hydrogen; sodium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Schotten-Baumann reaction / 6.2: Schotten-Baumann reaction;
DOI:10.1016/j.bmc.2004.10.060