(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal

Base Information

• Chemical Name: (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal
• CAS No.: 135513-03-0
• Molecular Formula: C₃₁H₃₀O₂
• Molecular Weight: 434.578
• Mol file: 135513-03-0.mol

Synonyms:(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal

Chemical Property of (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal

There total 12 articles about (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal 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: 45.0%

(R,R)-hydroxybenzoin (52340-78-0) + 1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (135513-01-8,135559-59-0) → (1R,4S,5S,8R)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal (135513-03-0) + (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal (135513-03-0)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; at 80 ℃; for 12h; Yield given;

DOI:10.1021/jo00018a008

Reference yield: 45.0%

(R,R)-hydroxybenzoin (52340-78-0) + 1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (135513-01-8,135559-59-0) → (1R,4S,5S,8R)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal (135513-03-0) + (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal (135513-03-0)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; at 80 ℃; for 12h; Yield given;

DOI:10.1021/jo00018a008

Reference yield:

1α,4α,4aβ,10aα,5β,8β,8aα,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione (78548-82-0) → (1R,4S,5S,8R)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal (135513-03-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / H₂ / Pd/C / ethyl acetate / 18 h / 31028.9 Torr / Ambient temperature

2: NaBH₄ / methanol / 8 h / Ambient temperature

3: 57 percent / H₃PO₄ / H₂O / 16 h / 110 °C

4: 87 percent / TiCl₄ / CH₂Cl₂ / -15 - 0 °C

5: 30 percent / pyridinium p-toluenesulfonate / benzene / 18 h / Heating

With sodium tetrahydroborate; phosphoric acid; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate; benzene;

DOI:10.1016/S0040-4020(97)00729-1

upstream raw materials:

(R,R)-hydroxybenzoin

1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde

1α,4α,4aβ,10aα,5β,8β,8aα,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione

endo-cis-anti-cis-endo-1,2,3,4,4a,5,6,7,8,8a,9a,10a-Dodecahydro-1,4:5,8-dimethanoanthracene-9,10-dione