(1S,8R,10R,11R)-1,11-Dihydroxy-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.0^2,7]dodeca-2,4,6-triene-5-carboxylic acid 2,4-dimethoxy-benzylamide

Base Information

• Chemical Name: (1S,8R,10R,11R)-1,11-Dihydroxy-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.0^2,7]dodeca-2,4,6-triene-5-carboxylic acid 2,4-dimethoxy-benzylamide
• CAS No.: 96867-02-6
• Molecular Formula: C₂₄H₂₉NO₈
• Molecular Weight: 459.496

Synonyms:(1S,8R,10R,11R)-1,11-Dihydroxy-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.0^2,7]dodeca-2,4,6-triene-5-carboxylic acid 2,4-dimethoxy-benzylamide

Chemical Property of (1S,8R,10R,11R)-1,11-Dihydroxy-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.0^2,7]dodeca-2,4,6-triene-5-carboxylic acid 2,4-dimethoxy-benzylamide

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (1S,8R,10R,11R)-1,11-Dihydroxy-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.0^2,7]dodeca-2,4,6-triene-5-carboxylic acid 2,4-dimethoxy-benzylamide

There total 9 articles about (1S,8R,10R,11R)-1,11-Dihydroxy-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.0^2,7]dodeca-2,4,6-triene-5-carboxylic acid 2,4-dimethoxy-benzylamide 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: 71.0%

carbon monoxide (201230-82-2) + 2,4-Dimethoxybenzylamine (20781-20-8) + (1S,8R,10R,11R)-5-Bromo-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.02,7]dodeca-2,4,6-triene-1,11-diol (96867-01-5) → (1S,8R,10R,11R)-1,11-Dihydroxy-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.02,7]dodeca-2,4,6-triene-5-carboxylic acid 2,4-dimethoxy-benzylamide (96867-02-6)

Guidance literature:

bis-triphenylphosphine-palladium(II) chloride; at 90 ℃; for 14h; under 1.1 Torr;

DOI:10.1021/ja00301a050

Reference yield:

6-bromo-5,8-dimethoxy-1-tetralone (87338-27-0) → (1S,8R,10R,11R)-1,11-Dihydroxy-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.02,7]dodeca-2,4,6-triene-5-carboxylic acid 2,4-dimethoxy-benzylamide (96867-02-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) LiN(i-Pr)2; 2.) m-ClC₆H₄CO₃H / 2.) CH₂Cl₂, 0 deg C

2: 86 percent / 18-O-6 crown/KCN / toluene / -30 °C

3: (i-Bu)2AlH / toluene / 4 h / -78 - 25 °C

4: 12M HCl / acetic acid; tetrahydrofuran; H₂O / 7 h / 65 °C

5: 84 percent / conc. HCl / acetic acid; tetrahydrofuran; H₂O / 6 h / 60 °C

6: 80 percent / tetrahydrofuran / 16 h / 25 °C

7: cyclohexene oxide, Br₂, NBS / AIBN / CCl₄ / 0.75 h / 10 °C / Irradiation

8: 53 percent / AgClO₄ / tetrahydrofuran / 1 h / 0 °C

9: 71 percent / (Ph₃P)2Cl₂Pd / 14 h / 90 °C / 1.1 Torr

With hydrogenchloride; N-Bromosuccinimide; bromine; silver perchlorate; cyclohexane-1,2-epoxide; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; potassium cyanide; bis-triphenylphosphine-palladium(II) chloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; tetrachloromethane; water; acetic acid; toluene;

DOI:10.1021/ja00301a050

Reference yield:

(1S,2S)-6-Bromo-1-((R)-1-hydroxy-ethyl)-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalene-1,2-diol (96866-93-2) → (1S,8R,10R,11R)-1,11-Dihydroxy-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.02,7]dodeca-2,4,6-triene-5-carboxylic acid 2,4-dimethoxy-benzylamide (96867-02-6)

Guidance literature:

Multi-step reaction with 3 steps

1: cyclohexene oxide, Br₂, NBS / AIBN / CCl₄ / 0.75 h / 10 °C / Irradiation

2: 53 percent / AgClO₄ / tetrahydrofuran / 1 h / 0 °C

3: 71 percent / (Ph₃P)2Cl₂Pd / 14 h / 90 °C / 1.1 Torr

With N-Bromosuccinimide; bromine; silver perchlorate; cyclohexane-1,2-epoxide; bis-triphenylphosphine-palladium(II) chloride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; tetrachloromethane;

DOI:10.1021/ja00301a050

upstream raw materials:

carbon monoxide

2,4-Dimethoxybenzylamine

(1S,8R,10R,11R)-5-Bromo-3,6-dimethoxy-10-methyl-9-oxa-tricyclo[6.2.2.0^2,7]dodeca-2,4,6-triene-1,11-diol

6-bromo-5,8-dimethoxy-1-tetralone

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