(S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dione

Base Information

• Chemical Name: (S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dione
• CAS No.: 198268-10-9
• Molecular Formula: C₂₂H₂₉NO₄S
• Molecular Weight: 403.543

Synonyms:(S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dione

Chemical Property of (S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dione

Chemical Property:

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Technology Process of (S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dione

There total 2 articles about (S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-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: 87.0%

(2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) + 5-(benzyloxy)pent-2-enoic acid chloride (1029569-92-3) → (S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-3,3-dione (198268-10-9)

Guidance literature:

(2R)-bornane-10,2-sultam; With sodium hydride; In toluene; at 23 ℃; for 2h;

5-(benzyloxy)pent-2-enoic acid chloride; In toluene; at 23 ℃; for 2h;

DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5

Reference yield:

5-benzyloxy-2-(E)-pentenocarboxylic acid (128217-54-9) → (S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-3,3-dione (198268-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl chloride; DMF / CH₂Cl₂ / 3 h / 0 - 23 °C

2.1: NaH / toluene / 2 h / 23 °C

2.2: 87 percent / toluene / 2 h / 23 °C

With oxalyl dichloride; sodium hydride; N,N-dimethyl-formamide; In dichloromethane; toluene; 1.1: Substitution / 2.1: deprotonation / 2.2: Acylation;

DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5

Reference yield: 71.0%

chloroformic acid ethyl ester (541-41-3) + (S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-3,3-dione (198268-10-9) + diazomethyl-trimethyl-silane (18107-18-1) → ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{1-[(S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]dec-4-yl]-carbonyl}-4,5-dihydropyrazole-1-carboxylate + ethyl (4R,5R)-4-[2-(benzyloxy)ethyl]-5-{1-[(S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]dec-4-yl]-carbonyl}-4,5-dihydropyrazole-1-carboxylate (198268-11-0)

Guidance literature:

(S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dione; diazomethyl-trimethyl-silane; With molecular sieve; In hexane; dichloromethane; at 23 ℃; for 90h;

chloroformic acid ethyl ester; With silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5

upstream raw materials:

(2R)-bornane-10,2-sultam

5-(benzyloxy)pent-2-enoic acid chloride

5-benzyloxy-2-(E)-pentenocarboxylic acid

Downstream raw materials:

ethyl (4R,5R)-4-[2-(benzyloxy)ethyl]-5-{1-[(S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl]-carbonyl}-4,5-dihydropyrazole-1-carboxylate

(1S,8aS)-1-[2-(benzyloxy)ethyl]-1,5,8,8a-tetrahydro-pyrazolo[1,5-a]pyridine

ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-1-carboxylate

ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-5-formyl-4,5-dihydropyrazole-1-carboxylate

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