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

Base Information

Chemical Name:(2S,5S,4R,5S)-2-(3-azidopropyl)-4-[(1S,2S)-2-hydroxy-1,2-diphenylethoxy]-3-(2-hydroxy-6-methoxyhexyl)-5-methylcyclohexanone
CAS No.:1274891-90-5
Molecular Formula:C₃₁H₄₃N₃O₅
Molecular Weight:537.7
Hs Code.:

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

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

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

There total 5 articles about (2S,5S,4R,5S)-2-(3-azidopropyl)-4-[(1S,2S)-2-hydroxy-1,2-diphenylethoxy]-3-(2-hydroxy-6-methoxyhexyl)-5-methylcyclohexanone 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: 45.0%

: 1274891-89-2
2-{(1S,2S,5S,6R)-2-(3-azidopropyl)-6-[(1S,2S)-2-hydroxy-1,2-diphenylethoxy]-5-methyl-3-oxocyclohexyl}acetaldehyde

: 634590-61-7
(4-methoxybutyl)magnesium chloride

: 1274891-90-5
(2S,5S,4R,5S)-2-(3-azidopropyl)-4-[(1S,2S)-2-hydroxy-1,2-diphenylethoxy]-3-(2-hydroxy-6-methoxyhexyl)-5-methylcyclohexanone

Guidance literature:: In tetrahydrofuran; at 0 - 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol200376z

Reference yield:

: 1225205-29-7
(1S,3S,4S,6S,8S)-6-methoxy-3,4-diphenyl-2,5-dioxabicyclo[6.4.0]dodec-11-en-10-one

: 1274891-90-5
(2S,5S,4R,5S)-2-(3-azidopropyl)-4-[(1S,2S)-2-hydroxy-1,2-diphenylethoxy]-3-(2-hydroxy-6-methoxyhexyl)-5-methylcyclohexanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

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

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

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

5.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With copper(l) iodide; sodium azide; water; potassium hexamethylsilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 2.1: Michael condensation / 5.1: Grignard reaction;
DOI:10.1021/ol200376z

Reference yield:

: 1274891-86-9
(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

: 1274891-90-5
(2S,5S,4R,5S)-2-(3-azidopropyl)-4-[(1S,2S)-2-hydroxy-1,2-diphenylethoxy]-3-(2-hydroxy-6-methoxyhexyl)-5-methylcyclohexanone

Guidance literature:: Multi-step reaction with 4 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

4: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

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 / 4: Grignard reaction;
DOI:10.1021/ol200376z