(9S,13S)-5,6,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-8-hydroxy-3-methoxymorphinan-7-one

Base Information

Chemical Name:(9S,13S)-5,6,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-8-hydroxy-3-methoxymorphinan-7-one
CAS No.:160694-00-8
Molecular Formula:C₃₂H₂₉NO₆
Molecular Weight:523.585
Hs Code.:

Synonyms:(9S,13S)-5,6,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-8-hydroxy-3-methoxymorphinan-7-one

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Chemical Property of (9S,13S)-5,6,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-8-hydroxy-3-methoxymorphinan-7-one

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Technology Process of (9S,13S)-5,6,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-8-hydroxy-3-methoxymorphinan-7-one

There total 11 articles about (9S,13S)-5,6,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-8-hydroxy-3-methoxymorphinan-7-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: 89.0%

: 160693-99-2
(8S,9S,13R,14S)-5,6-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-8-hydroxy-3-methoxymorphinan-7-one

: 160694-00-8
(9S,13S)-5,6,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-8-hydroxy-3-methoxymorphinan-7-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃;
DOI:10.1039/c39940002707

Reference yield:

: 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide

: 160694-00-8
(9S,13S)-5,6,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-8-hydroxy-3-methoxymorphinan-7-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1) MeOH, 2) NaHCO₃ / 1) reflux, 1 h, 2) r.t., 0.5 h

2: 91 percent / Li(sBu)3BH / tetrahydrofuran / 3 h / -78 °C

3: 96 percent / nBu₃P / tetrahydrofuran / 4 h / Ambient temperature

4: 89 percent / aq. H₂O₂ / tetrahydrofuran / 21 h / Ambient temperature

5: 89 percent / (COCl)2, DMSO / CH₂Cl₂ / -78 °C

With methanol; oxalyl dichloride; tributylphosphine; dihydrogen peroxide; L-Selectride; sodium hydrogencarbonate; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c39940002707

Reference yield:

: 160693-95-8
O-Benzylsinomenine

: 160694-00-8
(9S,13S)-5,6,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-8-hydroxy-3-methoxymorphinan-7-one

Guidance literature:: Multi-step reaction with 6 steps

1: NaHCO₃ / 1,2-dichloro-ethane / 2 h / Heating

2: 1) MeOH, 2) NaHCO₃ / 1) reflux, 1 h, 2) r.t., 0.5 h

3: 91 percent / Li(sBu)3BH / tetrahydrofuran / 3 h / -78 °C

4: 96 percent / nBu₃P / tetrahydrofuran / 4 h / Ambient temperature

5: 89 percent / aq. H₂O₂ / tetrahydrofuran / 21 h / Ambient temperature

6: 89 percent / (COCl)2, DMSO / CH₂Cl₂ / -78 °C

With methanol; oxalyl dichloride; tributylphosphine; dihydrogen peroxide; L-Selectride; sodium hydrogencarbonate; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1039/c39940002707