(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

Base Information

Chemical Name:(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
CAS No.:910324-29-7
Molecular Formula:C₂₂H₂₂O₈
Molecular Weight:414.412
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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:

: 910324-28-6
(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

: 910324-29-7
(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

Guidance literature:: (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; With ozone; In dichloromethane; at -78 ℃; for 0.5h;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/ol061390i

Reference yield:

: 676451-02-8
(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

: 910324-29-7
(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

Guidance literature:: Multi-step reaction with 7 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

4.1: BaCO₃; N-bromosuccinimide / CCl₄ / 1 h / Heating

5.1: 66 percent / KI / dimethylformamide / 12 h / 50 °C

6.1: 94 percent / AgF; pyridine / 12 h / 20 °C

7.1: O₃ / CH₂Cl₂ / 0.5 h / -78 °C

7.2: 100 mg / Me₂S / CH₂Cl₂ / -78 - 20 °C

With pyridine; potassium hydroxide; N-Bromosuccinimide; silver fluoride; ozone; barium carbonate; potassium iodide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.3: Jones oxidation;
DOI:10.1021/ol061390i

Reference yield:

: 910324-25-3
(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

: 910324-29-7
(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

Guidance literature:: Multi-step reaction with 4 steps

1.1: BaCO₃; N-bromosuccinimide / CCl₄ / 1 h / Heating

2.1: 66 percent / KI / dimethylformamide / 12 h / 50 °C

3.1: 94 percent / AgF; pyridine / 12 h / 20 °C

4.1: O₃ / CH₂Cl₂ / 0.5 h / -78 °C

4.2: 100 mg / Me₂S / CH₂Cl₂ / -78 - 20 °C

With pyridine; N-Bromosuccinimide; silver fluoride; ozone; barium carbonate; potassium iodide; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol061390i