(2R,2aS,3S,4aR,7R,8aS,8bS,11aS)-3-Methoxy-10-methyl-11-oxo-7-phenyl-1,2,2a,3,4a,8a,11,11a-octahydro-5H-4,6,8-trioxa-pentaleno[6a,1-a]naphthalene-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,2aS,3S,4aR,7R,8aS,8bS,11aS)-3-Methoxy-10-methyl-11-oxo-7-phenyl-1,2,2a,3,4a,8a,11,11a-octahydro-5H-4,6,8-trioxa-pentaleno[6a,1-a]naphthalene-2-carboxylic acid methyl ester
• CAS No.: 910324-25-3
• Molecular Formula: C₂₃H₂₆O₇
• Molecular Weight: 414.455

Synonyms:

Chemical Property of (2R,2aS,3S,4aR,7R,8aS,8bS,11aS)-3-Methoxy-10-methyl-11-oxo-7-phenyl-1,2,2a,3,4a,8a,11,11a-octahydro-5H-4,6,8-trioxa-pentaleno[6a,1-a]naphthalene-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,2aS,3S,4aR,7R,8aS,8bS,11aS)-3-Methoxy-10-methyl-11-oxo-7-phenyl-1,2,2a,3,4a,8a,11,11a-octahydro-5H-4,6,8-trioxa-pentaleno[6a,1-a]naphthalene-2-carboxylic acid methyl ester

There total 4 articles about (2R,2aS,3S,4aR,7R,8aS,8bS,11aS)-3-Methoxy-10-methyl-11-oxo-7-phenyl-1,2,2a,3,4a,8a,11,11a-octahydro-5H-4,6,8-trioxa-pentaleno[6a,1-a]naphthalene-2-carboxylic acid methyl ester 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:

(1S,2S,4R,7R,9S,10S,11S,13R)-1,13-dicarbaldehyde-9-methoxy-4-phenyl-3,5,8-trioxatricyclo[8.3.01,10.02.7]tridecane-11-carboxylic acid methyl ester (676451-02-8) → (2R,2aS,3S,4aR,7R,8aS,8bS,11aS)-3-Methoxy-10-methyl-11-oxo-7-phenyl-1,2,2a,3,4a,8a,11,11a-octahydro-5H-4,6,8-trioxa-pentaleno[6a,1-a]naphthalene-2-carboxylic acid methyl ester (910324-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 0.83 h / -30 °C

1.2: aq. LiOH / tetrahydrofuran / 12 h / 20 °C

1.3: Jones reagent / acetone / 0.25 h / 0 °C

2.1: KOH / methanol / 6 h / Heating

3.1: 642 mg / diethyl ether; CH₂Cl₂ / 0.5 h / 0 °C

With potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.3: Jones oxidation;

DOI:10.1021/ol061390i

Reference yield:

(2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid (910324-24-2) → (2R,2aS,3S,4aR,7R,8aS,8bS,11aS)-3-Methoxy-10-methyl-11-oxo-7-phenyl-1,2,2a,3,4a,8a,11,11a-octahydro-5H-4,6,8-trioxa-pentaleno[6a,1-a]naphthalene-2-carboxylic acid methyl ester (910324-25-3)

Guidance literature:

Multi-step reaction with 2 steps

1: KOH / methanol / 6 h / Heating

2: 642 mg / diethyl ether; CH₂Cl₂ / 0.5 h / 0 °C

With potassium hydroxide; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/ol061390i

Reference yield:

(1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.02,11.03,8]pentadec-13-ene-2-carbaldehyde (193271-77-1) → (2R,2aS,3S,4aR,7R,8aS,8bS,11aS)-3-Methoxy-10-methyl-11-oxo-7-phenyl-1,2,2a,3,4a,8a,11,11a-octahydro-5H-4,6,8-trioxa-pentaleno[6a,1-a]naphthalene-2-carboxylic acid methyl ester (910324-25-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: O₃; NaHCO₃ / CH₂Cl₂ / -78 °C

1.2: 92.3 percent / Ac₂O; Et₃N / CH₂Cl₂ / 1 h / 20 °C

2.1: tetrahydrofuran / 0.83 h / -30 °C

2.2: aq. LiOH / tetrahydrofuran / 12 h / 20 °C

2.3: Jones reagent / acetone / 0.25 h / 0 °C

3.1: KOH / methanol / 6 h / Heating

4.1: 642 mg / diethyl ether; CH₂Cl₂ / 0.5 h / 0 °C

With potassium hydroxide; sodium hydrogencarbonate; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.3: Jones oxidation;

DOI:10.1021/ol061390i

upstream raw materials:

diazomethane

(1S,2S,4R,7R,9S,10S,11S,13R)-1,13-dicarbaldehyde-9-methoxy-4-phenyl-3,5,8-trioxatricyclo[8.3.0^1,10.0^2.7]tridecane-11-carboxylic acid methyl ester

(2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid

(1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde

Downstream raw materials:

(1S,2S,4S,4aS,5R,6aS,9aS)-1-Benzoyloxy-2-bromomethyl-4-methoxy-8-methyl-7-oxo-1,2,4,4a,5,6,6a,7-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester

(1S,4S,4aS,5R,6aS,9aS)-1-Benzoyloxy-4-methoxy-8-methyl-2,7-dioxo-1,2,4,4a,5,6,6a,7-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester

(1S,4S,4aS,5R,6aS,9aS)-1-Benzoyloxy-4-methoxy-8-methyl-2-methylene-7-oxo-1,2,4,4a,5,6,6a,7-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester

(1S,2S,4S,4aS,5R,6aS,9aS)-1-Benzoyloxy-2-iodomethyl-4-methoxy-8-methyl-7-oxo-1,2,4,4a,5,6,6a,7-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester

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