((1S,2S,6R,8S,9S,12R)-2-Acetoxy-3-methoxy-5-oxo-8-phenylselanyl-10-oxa-tricyclo[7.2.1.0^1,6]dodec-3-en-12-yl)-acetic acid methyl ester

Base Information

• Chemical Name: ((1S,2S,6R,8S,9S,12R)-2-Acetoxy-3-methoxy-5-oxo-8-phenylselanyl-10-oxa-tricyclo[7.2.1.0^1,6]dodec-3-en-12-yl)-acetic acid methyl ester
• CAS No.: 97654-94-9
• Molecular Formula: C₂₃H₂₆O₇Se
• Molecular Weight: 493.415

Synonyms:((1S,2S,6R,8S,9S,12R)-2-Acetoxy-3-methoxy-5-oxo-8-phenylselanyl-10-oxa-tricyclo[7.2.1.0^1,6]dodec-3-en-12-yl)-acetic acid methyl ester

Chemical Property of ((1S,2S,6R,8S,9S,12R)-2-Acetoxy-3-methoxy-5-oxo-8-phenylselanyl-10-oxa-tricyclo[7.2.1.0^1,6]dodec-3-en-12-yl)-acetic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of ((1S,2S,6R,8S,9S,12R)-2-Acetoxy-3-methoxy-5-oxo-8-phenylselanyl-10-oxa-tricyclo[7.2.1.0^1,6]dodec-3-en-12-yl)-acetic acid methyl ester

There total 6 articles about ((1S,2S,6R,8S,9S,12R)-2-Acetoxy-3-methoxy-5-oxo-8-phenylselanyl-10-oxa-tricyclo[7.2.1.0^1,6]dodec-3-en-12-yl)-acetic acid methyl 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: 79.0%

Phenylselenyl chloride (5707-04-0) + ((1R,4aS,8R,8aR)-8-Acetoxy-8a-hydroxymethyl-7-methoxy-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl)-acetic acid methyl ester (97654-93-8) → ((1S,2S,6R,8S,9S,12R)-2-Acetoxy-3-methoxy-5-oxo-8-phenylselanyl-10-oxa-tricyclo[7.2.1.01,6]dodec-3-en-12-yl)-acetic acid methyl ester (97654-94-9)

Guidance literature:

With potassium carbonate; In dichloromethane; for 4h;

DOI:10.1021/jo00221a019

Reference yield:

3,5-Hexadiensaeure-methylester (40338-61-2) → ((1S,2S,6R,8S,9S,12R)-2-Acetoxy-3-methoxy-5-oxo-8-phenylselanyl-10-oxa-tricyclo[7.2.1.01,6]dodec-3-en-12-yl)-acetic acid methyl ester (97654-94-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / 24 h / 55 °C

2: TsOH / CH₂Cl₂ / 0.33 h / 0 °C

3: 99 percent / NaBH₄ / methanol / 0.5 h / -40 °C

4: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

5: 1 N aq. HCl / methanol / 1 h / Ambient temperature

6: 79 percent / K₂CO₃ / CH₂Cl₂ / 4 h

With hydrogenchloride; dmap; sodium tetrahydroborate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00221a019

Reference yield:

((1S,4aR,8aS)-8a-Hydroxymethyl-7-methoxy-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl)-acetic acid methyl ester (97654-83-6) → ((1S,2S,6R,8S,9S,12R)-2-Acetoxy-3-methoxy-5-oxo-8-phenylselanyl-10-oxa-tricyclo[7.2.1.01,6]dodec-3-en-12-yl)-acetic acid methyl ester (97654-94-9)

Guidance literature:

Multi-step reaction with 5 steps

1: TsOH / CH₂Cl₂ / 0.33 h / 0 °C

2: 99 percent / NaBH₄ / methanol / 0.5 h / -40 °C

3: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

4: 1 N aq. HCl / methanol / 1 h / Ambient temperature

5: 79 percent / K₂CO₃ / CH₂Cl₂ / 4 h

With hydrogenchloride; dmap; sodium tetrahydroborate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00221a019

upstream raw materials:

Phenylselenyl chloride

((1R,4aS,8R,8aR)-8-Acetoxy-8a-hydroxymethyl-7-methoxy-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl)-acetic acid methyl ester

3,5-Hexadiensaeure-methylester

((1S,4aR,8aS)-8a-Hydroxymethyl-7-methoxy-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl)-acetic acid methyl ester

Downstream raw materials:

C₂₀H₂₀O₅Se

C₂₀H₂₀O₄Se

C₂₀H₂₀O₃Se

((1S,2S,6R,8S,9S,12R)-2-Hydroxy-3-methoxy-5-oxo-8-phenylselanyl-10-oxa-tricyclo[7.2.1.0^1,6]dodec-3-en-12-yl)-acetic acid

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