(3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde

Base Information

• Chemical Name: (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde
• CAS No.: 186415-74-7
• Molecular Formula: C₄₄H₆₀O₃
• Molecular Weight: 636.959
• Mol file: 186415-74-7.mol

Synonyms:(3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde

Chemical Property of (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde

There total 9 articles about (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-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: 83.0%

((3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-4-yl)-methanol (186415-73-6) → (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde (186415-74-7)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 3h;

DOI:10.1248/cpb.45.877

Reference yield:

soyasapogenol B (124862-79-9,595-15-3) → (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde (186415-74-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / DL-camphorsulfonic acid / 45 °C

2: 56 percent / sodium hydride / dimethylformamide / 2 h

3: 6 percent / diisobutylaluminiumhydride / toluene / 2 h / 0 °C

4: 82 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 °C

With oxalyl dichloride; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene; 4: Swern oxidation;

DOI:10.1016/j.bmc.2005.04.074

Reference yield:

(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-4,6a,6b,8a,11,11,14b-Heptamethyl-4-trityloxymethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-3,9-diol (83689-13-8) → (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde (186415-74-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / NaH / dimethylformamide / 5 h / 40 °C

2: 72 percent / HCl / methanol; acetone / 0.5 h / Heating

3: 82 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 °C

With hydrogenchloride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 3: Swern oxidation;

DOI:10.1016/j.bmc.2005.04.074

upstream raw materials:

((3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-4-yl)-methanol

benzaldehyde dimethyl acetal

benzyl bromide

soyasapogenol B

Downstream raw materials:

3β,22β-dibenzyloxyolean-12-ene

(3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carboxylic acid

N-n-butyl-3β,22β-dibenzyloxyolean-12-ene-24-amide

sophoradiol