2,2-Dimethyl-propionic acid (1R,6R,7R,8S,9R)-7-benzyloxy-9-methyl-4,12-dioxo-10-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-8-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (1R,6R,7R,8S,9R)-7-benzyloxy-9-methyl-4,12-dioxo-10-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-8-yl ester
• CAS No.: 98611-68-8
• Molecular Formula: C₂₄H₂₈O₆
• Molecular Weight: 412.483

Synonyms:2,2-Dimethyl-propionic acid (1R,6R,7R,8S,9R)-7-benzyloxy-9-methyl-4,12-dioxo-10-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-8-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (1R,6R,7R,8S,9R)-7-benzyloxy-9-methyl-4,12-dioxo-10-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-8-yl ester

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Technology Process of 2,2-Dimethyl-propionic acid (1R,6R,7R,8S,9R)-7-benzyloxy-9-methyl-4,12-dioxo-10-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-8-yl ester

There total 12 articles about 2,2-Dimethyl-propionic acid (1R,6R,7R,8S,9R)-7-benzyloxy-9-methyl-4,12-dioxo-10-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-8-yl 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: 70.0%

2,2-Dimethyl-propionic acid (1R,2S,6R,7R,8S,9R)-7-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-9-methyl-12-oxo-10-oxa-tricyclo[7.2.1.01,6]dodec-4-en-8-yl ester (98611-62-2) → 2,2-Dimethyl-propionic acid (1R,6R,7R,8S,9R)-7-benzyloxy-9-methyl-4,12-dioxo-10-oxa-tricyclo[7.2.1.01,6]dodec-2-en-8-yl ester (98611-68-8)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; water;

DOI:10.1021/jo00220a064

Reference yield:

pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (1R,6R,7R,8S,9R)-7-benzyloxy-9-methyl-4,12-dioxo-10-oxa-tricyclo[7.2.1.01,6]dodec-2-en-8-yl ester (98611-68-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 4-DMAP

2: Et₃N / diethyl ether

3: L-selectride / diethyl ether / -78 °C

4: NaH, EtOH

5: K₂CO₃ / acetone

6: Al(CH₃)3 / CH₂Cl₂ / -20 °C

7: 70 percent / H₂SO₄ / dioxane; H₂O

With dmap; ethanol; sulfuric acid; trimethylaluminum; L-Selectride; sodium hydride; potassium carbonate; triethylamine; In 1,4-dioxane; diethyl ether; dichloromethane; water; acetone;

DOI:10.1021/jo00220a064

Reference yield:

(2S,3S)-2-Benzyloxy-3-hydroxy-3-((R)-2-methyl-3-oxo-2,3-dihydro-furan-2-yl)-propionaldehyde (98611-69-9) → 2,2-Dimethyl-propionic acid (1R,6R,7R,8S,9R)-7-benzyloxy-9-methyl-4,12-dioxo-10-oxa-tricyclo[7.2.1.01,6]dodec-2-en-8-yl ester (98611-68-8)

Guidance literature:

Multi-step reaction with 8 steps

1: toluene / 12 h / 40 °C

2: 4-DMAP

3: Et₃N / diethyl ether

4: L-selectride / diethyl ether / -78 °C

5: NaH, EtOH

6: K₂CO₃ / acetone

7: Al(CH₃)3 / CH₂Cl₂ / -20 °C

8: 70 percent / H₂SO₄ / dioxane; H₂O

With dmap; ethanol; sulfuric acid; trimethylaluminum; L-Selectride; sodium hydride; potassium carbonate; triethylamine; In 1,4-dioxane; diethyl ether; dichloromethane; water; acetone; toluene;

DOI:10.1021/jo00220a064

upstream raw materials:

2,2-Dimethyl-propionic acid (1R,2S,6R,7R,8S,9R)-7-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-9-methyl-12-oxo-10-oxa-tricyclo[7.2.1.0^1,6]dodec-4-en-8-yl ester

pivaloyl chloride

(2S,3S)-2-Benzyloxy-3-hydroxy-3-((R)-2-methyl-3-oxo-2,3-dihydro-furan-2-yl)-propionaldehyde

(R)-2-((E)-(1S,2R)-2-Benzyloxy-1-hydroxy-5-oxo-hex-3-enyl)-2-methyl-furan-3-one

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