(5S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.0^1,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione

Base Information

• Chemical Name: (5S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.0^1,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione
• CAS No.: 863984-93-4
• Molecular Formula: C₃₂H₃₅N₃O₅S
• Molecular Weight: 573.713

Synonyms:(5S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.0^1,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione

Chemical Property of (5S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.0^1,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione

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Technology Process of (5S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.0^1,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione

There total 2 articles about (5S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.0^1,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione 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: 37.0%

1,3-dibenzyl-5-methyleneimidazolidine-2,4-dione (120803-26-1) + N-(2-butynoyl)bornane-10,2-sultam (114951-08-5) → (5R)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione + (5S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione (863984-93-4)

Guidance literature:

With tributylphosphine; In benzene;

DOI:10.1021/jo050827h

Reference yield:

benzyl bromide (100-39-0) → (5S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione (863984-93-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: K₂CO₃ / dimethylformamide / 40 °C

1.2: 83 percent / dimethylformamide / 3 h / 40 - 50 °C

2.1: 37 percent / tributylphosphine / benzene

With tributylphosphine; potassium carbonate; In N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo050827h

Reference yield: 90.0%

(5S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione (863984-93-4) → (5R,7S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-8-ene-2,4-dione (863985-09-5)

Guidance literature:

(5S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.0^1,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-7-ene-2,4-dione; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 1h;

With acetic acid; at -78 - 20 ℃;

DOI:10.1021/jo050827h

upstream raw materials:

1,3-dibenzyl-5-methyleneimidazolidine-2,4-dione

N-(2-butynoyl)bornane-10,2-sultam

benzyl bromide

Downstream raw materials:

(5R,7S)-1,3-dibenzyl-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-azatricyclo[5.2.1.0^1,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-8-ene-2,4-dione

(5R,7S,8S,9R)-1,3-dibenzyl-8,9-dihydroxy-7-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3-thio-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl]-1,3-diaza-spiro[4.4]non-8-ene-2,4-dione

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