methyl (2Z)-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-methoxy-11-{(3E)-5-[(4-methoxyphenyl)amino]-4-methylpent-3-en-1-yl}-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-methylbut-2-enoate

Base Information

• Chemical Name: methyl (2Z)-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-methoxy-11-{(3E)-5-[(4-methoxyphenyl)amino]-4-methylpent-3-en-1-yl}-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-methylbut-2-enoate
• CAS No.: 1398663-17-6
• Molecular Formula: C₄₇H₅₅NO₉
• Molecular Weight: 777.955

Synonyms:

Chemical Property of methyl (2Z)-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-methoxy-11-{(3E)-5-[(4-methoxyphenyl)amino]-4-methylpent-3-en-1-yl}-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-methylbut-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2Z)-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-methoxy-11-{(3E)-5-[(4-methoxyphenyl)amino]-4-methylpent-3-en-1-yl}-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-methylbut-2-enoate

There total 3 articles about methyl (2Z)-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-methoxy-11-{(3E)-5-[(4-methoxyphenyl)amino]-4-methylpent-3-en-1-yl}-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-methylbut-2-enoate 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:

methyl 6-O-methylgambogate → methyl (2Z)-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-methoxy-11-{(3E)-5-[(4-methoxyphenyl)amino]-4-methylpent-3-en-1-yl}-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-methylbut-2-enoate (1398663-17-6)

Guidance literature:

Multi-step reaction with 3 steps

1: selenium(IV) oxide; tert.-butylhydroperoxide / dichloromethane / 19 h / 20 °C

2: N-chloro-succinimide / tetrachloromethane / 3 h / Reflux

3: acetone / 0.08 h / 80 °C / Microwave irradiation

With tert.-butylhydroperoxide; selenium(IV) oxide; N-chloro-succinimide; In tetrachloromethane; dichloromethane; acetone;

DOI:10.1002/cbdv.201100415

Reference yield:

methyl (2Z)-4-{(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-11-[(3E)-5-hydroxy-4-methylpent-3-en-1-yl]-8-methoxy-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl}-2-methylbut-2-enoate (1160999-20-1) → methyl (2Z)-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-methoxy-11-{(3E)-5-[(4-methoxyphenyl)amino]-4-methylpent-3-en-1-yl}-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-methylbut-2-enoate (1398663-17-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N-chloro-succinimide / tetrachloromethane / 3 h / Reflux

2: acetone / 0.08 h / 80 °C / Microwave irradiation

With N-chloro-succinimide; In tetrachloromethane; acetone;

DOI:10.1002/cbdv.201100415

Reference yield:

(-)-gambogic acid (2752-65-0) → methyl (2Z)-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-methoxy-11-{(3E)-5-[(4-methoxyphenyl)amino]-4-methylpent-3-en-1-yl}-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-methylbut-2-enoate (1398663-17-6)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / acetone / 144 h / 25 °C

2: selenium(IV) oxide; tert.-butylhydroperoxide / dichloromethane / 19 h / 20 °C

3: N-chloro-succinimide / tetrachloromethane / 3 h / Reflux

4: acetone / 0.08 h / 80 °C / Microwave irradiation

With tert.-butylhydroperoxide; selenium(IV) oxide; N-chloro-succinimide; potassium carbonate; In tetrachloromethane; dichloromethane; acetone;

DOI:10.1002/cbdv.201100415

upstream raw materials:

(-)-gambogic acid

methyl (2Z)-4-{(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-11-[(3E)-5-hydroxy-4-methylpent-3-en-1-yl]-8-methoxy-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl}-2-methylbut-2-enoate

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