(1'R,3a'R,4a'R,8a'R,9'R,9a'S)-1',8a'-dimethyl-3'-oxodecahydro-1'H-spiro[[1,3]dioxolane-2,6'-naphtho[2,3-c]furan]-9'-carbaldehyde

Base Information

• Chemical Name: (1'R,3a'R,4a'R,8a'R,9'R,9a'S)-1',8a'-dimethyl-3'-oxodecahydro-1'H-spiro[[1,3]dioxolane-2,6'-naphtho[2,3-c]furan]-9'-carbaldehyde
• CAS No.: 226916-29-6
• Molecular Formula: C16H22O5
• Molecular Weight: 294.34
• Mol file: 226916-29-6.mol

Synonyms:(1'R,3a'R,4a'R,8a'R,9'R,9a'S)-1',8a'-dimethyl-3'-oxodecahydro-1'H-spiro[[1,3]dioxolane-2,6'-naphtho[2,3-c]furan]-9'-carbaldehyde;(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

Chemical Property of (1'R,3a'R,4a'R,8a'R,9'R,9a'S)-1',8a'-dimethyl-3'-oxodecahydro-1'H-spiro[[1,3]dioxolane-2,6'-naphtho[2,3-c]furan]-9'-carbaldehyde

Chemical Property:

• PSA: 61.83000
• LogP: 1.54230

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1'R,3a'R,4a'R,8a'R,9'R,9a'S)-1',8a'-dimethyl-3'-oxodecahydro-1'H-spiro[[1,3]dioxolane-2,6'-naphtho[2,3-c]furan]-9'-carbaldehyde

There total 5 articles about (1'R,3a'R,4a'R,8a'R,9'R,9a'S)-1',8a'-dimethyl-3'-oxodecahydro-1'H-spiro[[1,3]dioxolane-2,6'-naphtho[2,3-c]furan]-9'-carbaldehyde 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:

C16H21O5Cl → (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 (226916-29-6)

Guidance literature:

With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 0 ℃; for 3h;

DOI:10.1021/jm061043e

Reference yield:

C23H26O6 → (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 (226916-29-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 13 g / DBU / tetrahydrofuran / 1 h

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

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

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

5: 450 mg / tributyltin hydride / Pd(Ph₃P)4 / toluene / 3 h / 0 °C

With thionyl chloride; hydrogen; tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; platinum(IV) oxide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethyl acetate; toluene;

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-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxaldehyde (226916-29-6)

Guidance literature:

Multi-step reaction with 4 steps

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

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

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

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

With thionyl chloride; hydrogen; tri-n-butyl-tin hydride; platinum(IV) oxide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethyl acetate; toluene;

DOI:10.1021/jm061043e

upstream raw materials:

(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

C₁₆H₂₀O₆

(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'-carboxylic acid

Downstream raw materials:

(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

Refernces