3α,18-isopropylidenedioxyaphidicolin

Base Information

• Chemical Name: 3α,18-isopropylidenedioxyaphidicolin
• CAS No.: 110386-56-6
• Molecular Formula: C₂₃H₃₈O₄
• Molecular Weight: 378.552
• Mol file: 110386-56-6.mol

Synonyms:

Chemical Property of 3α,18-isopropylidenedioxyaphidicolin

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Aphidicolin-3α,18-acetonide ≥98%(HPLC,1H-NMR) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3α,18-isopropylidenedioxyaphidicolin

There total 11 articles about 3α,18-isopropylidenedioxyaphidicolin 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: 100.0%

methyl 15β,16β-epoxy-3α,18-isopropylidenedioxyaphidicolane-16α-carboxylate (121741-52-4) → 3α,18-isopropylidenedioxyaphidicolin (110386-56-6,135502-20-4,135502-23-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

Reference yield: 35.0%

methyl 15β,16β-epoxy-3α,18-isopropylidenedioxyaphidicolane-16α-carboxylate (121741-52-4) → 3α,18-isopropylidenedioxyaphidicolin (110386-56-6,135502-20-4,135502-23-7) + 15β,16β-epoxy-3α,18-isopropylidenedioxyaphidicolan-17-ol (135404-87-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

Reference yield:

3α,18-isopropylidenedioxy-16-(trifluoromethylsulphonyloxy)-17-noraphidicol-15-ene (121741-50-2) → 3α,18-isopropylidenedioxyaphidicolin (110386-56-6,135502-20-4,135502-23-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / Et₃N / palladium(II)acetate, triphenylphosphine / dimethylformamide / 4 h

2: 90 percent / m-CPBA, disodium phosphate, bis(2-tert-butyl-3-hydroxy-4-methylphenyl)sulphide / CH₂Cl₂ / 8 h / Heating

3: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

With disodium hydrogenphosphate; lithium aluminium tetrahydride; bis(2-tert-butyl-3-hydroxy-4-methylphenyl)sulphide; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium diacetate; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

methyl 15β,16β-epoxy-3α,18-isopropylidenedioxyaphidicolane-16α-carboxylate

methyl 3α,18-isopropylidenedioxyaphidicol-15-ene-16-carboxylate

3α,18-isopropylidenedioxy-16-(trifluoromethylsulphonyloxy)-17-noraphidicol-15-ene

3α,18-isopropylidenedioxy-17-(p-tolylsulfonyloxy)aphidicolan-16β-ol

Downstream raw materials:

(+)-aphidicolin

(+)-aphidicolin 17-acetate