(2S)-2-[(-)-(5R,6R,7R,14S)-9R-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-[(ethoxycarbonyl)oxy]-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol

Base Information

Chemical Name:(2S)-2-[(-)-(5R,6R,7R,14S)-9R-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-[(ethoxycarbonyl)oxy]-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol
CAS No.:1252784-86-3
Molecular Formula:C₃₂H₄₅NO₆
Molecular Weight:539.712
Hs Code.:

Synonyms:(2S)-2-[(-)-(5R,6R,7R,14S)-9R-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-[(ethoxycarbonyl)oxy]-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol

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Chemical Property of (2S)-2-[(-)-(5R,6R,7R,14S)-9R-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-[(ethoxycarbonyl)oxy]-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol

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Technology Process of (2S)-2-[(-)-(5R,6R,7R,14S)-9R-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-[(ethoxycarbonyl)oxy]-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol

There total 11 articles about (2S)-2-[(-)-(5R,6R,7R,14S)-9R-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-[(ethoxycarbonyl)oxy]-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol 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: 66.0%

: 1252784-85-2
1-[(5α,7α)-17-(cyclopropylmethyl)-4,5-epoxy-3-[(ethoxycarbonyl)oxy]-18,19-dihydro-6-methoxy-6,14-ethenomorphinan-7-yl]ethanone

: 677-22-5
tert-butylmagnesium chloride

: 693242-77-2
Buprenorphine pivalate

: 1252784-86-3
(2S)-2-[(-)-(5R,6R,7R,14S)-9R-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-[(ethoxycarbonyl)oxy]-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol

: 52485-79-7
Buprenorphine

Guidance literature:: 1-[(5α,7α)-17-(cyclopropylmethyl)-4,5-epoxy-3-[(ethoxycarbonyl)oxy]-18,19-dihydro-6-methoxy-6,14-ethenomorphinan-7-yl]ethanone; tert-butylmagnesium chloride; In tetrahydrofuran; hexane; cyclohexane; toluene; at 20 ℃; for 0.583333h; Inert atmosphere;

With water; In tetrahydrofuran; hexane; cyclohexane; toluene; at 20 ℃;
DOI:10.1021/jo200567n

Reference yield: 15.0%

: 507-20-0
tertiary butyl chloride

: 1252784-85-2
1-[(5α,7α)-17-(cyclopropylmethyl)-4,5-epoxy-3-[(ethoxycarbonyl)oxy]-18,19-dihydro-6-methoxy-6,14-ethenomorphinan-7-yl]ethanone

: 693242-77-2
Buprenorphine pivalate

: 1252784-86-3
(2S)-2-[(-)-(5R,6R,7R,14S)-9R-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-[(ethoxycarbonyl)oxy]-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol

: 52485-79-7
Buprenorphine

Guidance literature:: tertiary butyl chloride; With magnesium; In tetrahydrofuran; cyclohexane;

1-[(5α,7α)-17-(cyclopropylmethyl)-4,5-epoxy-3-[(ethoxycarbonyl)oxy]-18,19-dihydro-6-methoxy-6,14-ethenomorphinan-7-yl]ethanone; In cyclohexane; toluene; at 20 ℃;

Reference yield:

: 467-04-9
oripavine

: 1252784-86-3
(2S)-2-[(-)-(5R,6R,7R,14S)-9R-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-[(ethoxycarbonyl)oxy]-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol

: 52485-79-7
Buprenorphine

Guidance literature:: Multi-step reaction with 6 steps

1.1: N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

1.3: 8 h / 80 °C / Inert atmosphere

2.1: 2,3,3,4,4,5-hexamethyl-2-hexanethiol; sodium ethanolate / dimethyl sulfoxide / 0.17 h / 100 °C / Inert atmosphere

3.1: triethylamine / ethyl acetate / 5 h / 20 °C / Inert atmosphere

4.1: water / 12 h / 80 °C

5.1: palladium 10% on activated carbon; hydrogen; tartaric acid / water / 16 h / 80 °C / 760.05 Torr

6.1: tetrahydrofuran; hexane; cyclohexane; toluene / Inert atmosphere

With 2,3,3,4,4,5-hexamethyl-2-hexanethiol; palladium 10% on activated carbon; hydrogen; sodium ethanolate; tartaric acid; triethylamine; In tetrahydrofuran; hexane; cyclohexane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; 4.1: Diels-Alder reaction / 6.1: Grignard reaction;
DOI:10.1021/jo200567n