(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

Base Information

• Chemical Name: (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
• CAS No.: 676451-02-8
• Molecular Formula: C₂₁H₂₄O₈
• Molecular Weight: 404.417

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 1 articles about (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 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: 92.3%

methanol (67-56-1) + (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) → (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)

Guidance literature:

methanol; (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; With sodium hydrogencarbonate; ozone; In dichloromethane; at -78 ℃;

With acetic anhydride; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol061390i

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) + ethylmagnesium bromide (925-90-6) → (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)

Guidance literature:

(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; ethylmagnesium bromide; In tetrahydrofuran; at -30 ℃; for 0.833333h;

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

With jones reagent; In acetone; at 0 ℃; for 0.25h;

DOI:10.1021/ol061390i

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) → (1S,4aS,5R,6aS,9aS)-1-Benzoyloxy-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 8 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

8.1: 100 percent / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 20 h / 0 - 20 °C

With pyridine; triethylsilane; potassium hydroxide; N-Bromosuccinimide; boron trifluoride diethyl etherate; 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

upstream raw materials:

methanol

(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:

(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

(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

(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

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