(1'R,3'aR,8'aS,9'S,9'aR)-1',3'a,5',7',8',8'a,9',9'a-octahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxylic acid phenylmethyl ester

Base Information

• Chemical Name: (1'R,3'aR,8'aS,9'S,9'aR)-1',3'a,5',7',8',8'a,9',9'a-octahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxylic acid phenylmethyl ester
• CAS No.: 226916-25-2
• Molecular Formula: C₂₃H₂₆O₆
• Molecular Weight: 398.456
• Mol file: 226916-25-2.mol

Synonyms:(1'R,3'aR,8'aS,9'S,9'aR)-1',3'a,5',7',8',8'a,9',9'a-octahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxylic acid phenylmethyl ester

Chemical Property of (1'R,3'aR,8'aS,9'S,9'aR)-1',3'a,5',7',8',8'a,9',9'a-octahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxylic acid phenylmethyl ester

Chemical Property:

Purity/Quality:

95%-98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,3'aR,8'aS,9'S,9'aR)-1',3'a,5',7',8',8'a,9',9'a-octahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxylic acid phenylmethyl ester

There total 1 articles about (1'R,3'aR,8'aS,9'S,9'aR)-1',3'a,5',7',8',8'a,9',9'a-octahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxylic acid phenylmethyl 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:

C23H26O6 → (1'R,3'aR,8'aS,9'S,9'aR)-1',3'a,5',7',8',8'a,9',9'a-octahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxylic acid phenylmethyl ester (226916-25-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 1h;

DOI:10.1021/jm061043e

Reference yield:

(1'R,3'aR,8'aS,9'S,9'aR)-1',3'a,5',7',8',8'a,9',9'a-octahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxylic acid phenylmethyl ester (226916-25-2) → (1'R,3'aR,4'aR,8'aR,9'S,9'aS)-decahydro-1'-methyl-9'-[(E)-2-[5-[3-(trifluoromethyl)phenyl]-2-pyridinyl]ethenyl]-spiro[1,3-dioxolane-26'(3'H)-naphtho[2,3-c]furan]-3'-one (226915-12-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / Pd/C / ethyl acetate / 1 h / 760.05 Torr

2.1: H₂ / PtO₂ / ethyl acetate / 16 h / 760.05 Torr

3.1: thionyl chloride / toluene / 16 h / 80 °C

4.1: 450 mg / tributyltin hydride / Pd(Ph₃P)4 / toluene / 3 h / 0 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

5.2: 83 percent / tetrahydrofuran; hexane / 2 h / 0 °C

With n-butyllithium; thionyl chloride; hydrogen; tri-n-butyl-tin hydride; platinum(IV) oxide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; ethyl acetate; toluene; 5.2: Horner-Emmons reaction;

DOI:10.1021/jm061043e

Reference yield:

(1'R,3'aR,8'aS,9'S,9'aR)-1',3'a,5',7',8',8'a,9',9'a-octahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxylic acid phenylmethyl ester (226916-25-2) → (3R,3aS,4S,4aR,8aR,9aR)-octahydro-3-methyl-4-[(E)-2-[5-[3-(trifluoromethyl)phenyl]-2-pyridinyl]ethenyl]naphtho[2,3-c]furan-1,7(3H,4H)-dione

Guidance literature:

Multi-step reaction with 6 steps

1.1: H₂ / Pd/C / ethyl acetate / 1 h / 760.05 Torr

2.1: H₂ / PtO₂ / ethyl acetate / 16 h / 760.05 Torr

3.1: thionyl chloride / toluene / 16 h / 80 °C

4.1: 450 mg / tributyltin hydride / Pd(Ph₃P)4 / toluene / 3 h / 0 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

5.2: 83 percent / tetrahydrofuran; hexane / 2 h / 0 °C

6.1: 99 percent / aq. HCl / acetone / 16 h / 50 °C

With hydrogenchloride; n-butyllithium; thionyl chloride; hydrogen; tri-n-butyl-tin hydride; platinum(IV) oxide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; ethyl acetate; acetone; toluene; 5.2: Horner-Emmons reaction;

DOI:10.1021/jm061043e

Downstream raw materials:

(1'R,3'aR,4'aR,8'aR,9'S,9'aS)-decahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxaldehyde

(1'R,3'aR,4'aR,8'aR,9'S,9'aS)-decahydro-1'-methyl-9'-[(E)-2-[5-[3-(trifluoromethyl)phenyl]-2-pyridinyl]ethenyl]-spiro[1,3-dioxolane-26'(3'H)-naphtho[2,3-c]furan]-3'-one