(6S,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-ol

Base Information

• Chemical Name: (6S,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-ol
• CAS No.: 160693-97-0
• Molecular Formula: C₃₃H₃₅NO₆
• Molecular Weight: 541.644
• Mol file: 160693-97-0.mol

Synonyms:(6S,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-ol

Chemical Property of (6S,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-ol

There total 7 articles about (6S,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-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: 91.0%

(9S,13R,14S)-7,8-Dehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-one (160693-96-9) → (6S,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-ol (160693-97-0)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1039/c39940002707

Reference yield: 50.0%

(9S,13R,14S)-7,8-Dehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-one (160693-96-9) → (6S,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-ol (160693-97-0) + (6R,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-ol (164738-86-7)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00119a037

Reference yield:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) → (6S,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-ol (160693-97-0)

Guidance literature:

Multi-step reaction with 2 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

With methanol; L-Selectride; sodium hydrogencarbonate; In tetrahydrofuran;

DOI:10.1039/c39940002707

upstream raw materials:

(9S,13R,14S)-7,8-Dehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxymorphinan-6-one

N-(Benzyloxycarbonyloxy)succinimide

O-Benzylsinomenine

benzyl alcohol

Downstream raw materials:

(6R,9S,13R,14S)-7,8-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,7-dimethoxy-6-<(2-nitrophenyl)seleno>morphinane

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

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