(3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine

Base Information

Chemical Name:(3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine
CAS No.:303766-95-2
Molecular Formula:C₃₈H₄₄ClN₃O₆
Molecular Weight:674.237
Hs Code.:

(3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine

Synonyms:(3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine

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Chemical Property of (3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine

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Technology Process of (3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine

There total 5 articles about (3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine 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:

: 18220-83-2
adamantan-1-ylacetaldehyde

: 303766-95-2
(3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine

Guidance literature:: Multi-step reaction with 5 steps

1.1: trifluoroacetic acid / CH₂Cl₂ / 23 h / 20 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

3.1: O₃ / methanol / -78 °C

3.2: Me₂S / methanol / 2 h / 20 °C

4.1: H₂ / 10percent Pd/C / methanol; tetrahydrofuran / 1 h / 20 °C

5.1: PyBroPy; i-Pr₂NEt / CH₂Cl₂ / 18 h / 20 °C

With dmap; PyBroPy; hydrogen; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; 1.1: Pictet-Spengler reaction / 2.1: Acetylation / 3.1: ozonolysis / 3.2: Reduction / 4.1: Hydrogenolysis / 5.1: Acylation;
DOI:10.1021/jm000960w

Reference yield:

: 1026151-76-7
(1R,3S)-1-Adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl ester

: 303766-95-2
(3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

2.1: O₃ / methanol / -78 °C

2.2: Me₂S / methanol / 2 h / 20 °C

3.1: H₂ / 10percent Pd/C / methanol; tetrahydrofuran / 1 h / 20 °C

4.1: PyBroPy; i-Pr₂NEt / CH₂Cl₂ / 18 h / 20 °C

With dmap; PyBroPy; hydrogen; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; 1.1: Acetylation / 2.1: ozonolysis / 2.2: Reduction / 3.1: Hydrogenolysis / 4.1: Acylation;
DOI:10.1021/jm000960w

Reference yield:

: (1R,3S)-2-Acetyl-1-adamantan-1-ylmethyl-9-(2-chloro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid benzyl ester

: 303766-95-2
(3R,5S)-4-acetyl-3-[(1-adamantyl)methyl]-1-(2-chlorobenzyl)-5-[(1S)-allyloxycarbonylethyl]aminocarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine

Guidance literature:: Multi-step reaction with 3 steps

1.1: O₃ / methanol / -78 °C

1.2: Me₂S / methanol / 2 h / 20 °C

2.1: H₂ / 10percent Pd/C / methanol; tetrahydrofuran / 1 h / 20 °C

3.1: PyBroPy; i-Pr₂NEt / CH₂Cl₂ / 18 h / 20 °C

With PyBroPy; hydrogen; ozone; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; 1.1: ozonolysis / 1.2: Reduction / 2.1: Hydrogenolysis / 3.1: Acylation;
DOI:10.1021/jm000960w