(1S,3S,4S,6S,8S,9S)-9-[3-chloro-1-propyl]-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one

Base Information

• Chemical Name: (1S,3S,4S,6S,8S,9S)-9-[3-chloro-1-propyl]-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one
• CAS No.: 1274891-86-9
• Molecular Formula: C₂₆H₂₉ClO₄
• Molecular Weight: 440.967
• Mol file: 1274891-86-9.mol

Synonyms:(1S,3S,4S,6S,8S,9S)-9-[3-chloro-1-propyl]-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one

Chemical Property of (1S,3S,4S,6S,8S,9S)-9-[3-chloro-1-propyl]-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4S,6S,8S,9S)-9-[3-chloro-1-propyl]-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one

There total 1 articles about (1S,3S,4S,6S,8S,9S)-9-[3-chloro-1-propyl]-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one 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: 48.0%

(1S,3S,4S,6S,8S)-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one (1225205-29-7) + 3-chloro-1-trifluoromethanesulfonyloxy-propane (122876-21-5) → C26H29ClO4 + (1S,3S,4S,6S,8S,9S)-9-[3-chloro-1-propyl]-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one (1274891-86-9)

Guidance literature:

(1S,3S,4S,6S,8S)-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

3-chloro-1-trifluoromethanesulfonyloxy-propane; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

DOI:10.1021/ol200376z

Reference yield:

(1S,3S,4S,6S,8S,9S)-9-[3-chloro-1-propyl]-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one (1274891-86-9) + methylmagnesium bromide (75-16-1) → C27H33ClO4

Guidance literature:

With copper(l) iodide; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol200376z

Reference yield:

(1S,3S,4S,6S,8S,9S)-9-[3-chloro-1-propyl]-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one (1274891-86-9) → 2-{(1S,2S,5S,6R)-2-(3-azidopropyl)-6-[(1S,2S)-2-hydroxy-1,2-diphenylethoxy]-5-methyl-3-oxocyclohexyl}acetaldehyde (1274891-89-2)

Guidance literature:

Multi-step reaction with 3 steps

1: copper(l) iodide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2: sodium azide; sodium iodide / N,N-dimethyl-formamide / 5 h / 60 °C / Inert atmosphere

3: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile / 6 h / 20 °C

With copper(l) iodide; sodium azide; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 1: Michael condensation;

DOI:10.1021/ol200376z

upstream raw materials:

(1S,3S,4S,6S,8S)-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one

3-chloro-1-trifluoromethanesulfonyloxy-propane

Downstream raw materials:

2-{(1S,2S,5S,6R)-2-(3-azidopropyl)-6-[(1S,2S)-2-hydroxy-1,2-diphenylethoxy]-5-methyl-3-oxocyclohexyl}acetaldehyde

(2S,5S,4R,5S)-2-(3-azidopropyl)-4-[(1S,2S)-2-hydroxy-1,2-diphenylethoxy]-3-(2-hydroxy-6-methoxyhexyl)-5-methylcyclohexanone

(1S,3S,4S,6S,8S,9S,12S)-9-[3-azidopropyl]-6-methoxy-12-methyl-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one