acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

Base Information

• Chemical Name: acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester
• CAS No.: 935263-69-7
• Molecular Formula: C₃₅H₄₈O₆
• Molecular Weight: 564.763
• Mol file: 935263-69-7.mol

Synonyms:acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

Chemical Property of acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

There total 18 articles about acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl 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:

acetic acid 2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-3-(1-methyl-2-oxo-ethyl)-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester → acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester (935263-69-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/ja070571s

Reference yield:

4-allyl-5-(4-hydroxy-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone (935263-71-1) → acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester (935263-69-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 88 percent / PPh₃; CBr₄ / acetonitrile / 20 °C

2: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C

3: 77 percent / NaBH₄; DPPP / Pd(OAc)2 / dimethylsulfoxide

4: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C

5: 93 percent / dimethyl sulfide; MgBr₂*Et₂O / CH₂Cl₂ / 0.67 h / 20 °C

6: (S,S)-N-[2-(2-PPh₂-benzoylamino)cyclohexyl]-2-PPh₂-benzamide / Pd₂dba3*CHCl₃ / CH₂Cl₂ / 20 °C

7: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation

8: Cs₂CO₃; Bu₄NI / dimethylformamide / 2 h

9: 8.7 mg / pyridine / 3 h / 20 °C

10: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C

11: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

12: 6.5 mg / NaBH₄ / CH₂Cl₂; methanol / 0.5 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); sodium tetrahydroborate; sodium periodate; AD-mix-α; dimethylsulfide; carbon tetrabromide; methanesulfonamide; 1,3-bis-(diphenylphosphino)propane; tetra-(n-butyl)ammonium iodide; caesium carbonate; triphenylphosphine; magnesium bromide; lithium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium diacetate; In tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 7: Claisen rearrangement / 10: Sharpless asymmetric dihydroxylation;

DOI:10.1021/ja070571s

Reference yield:

7-hydroxy-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one (935263-64-2) → acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester (935263-69-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / dimethyl sulfide; MgBr₂*Et₂O / CH₂Cl₂ / 0.67 h / 20 °C

2: (S,S)-N-[2-(2-PPh₂-benzoylamino)cyclohexyl]-2-PPh₂-benzamide / Pd₂dba3*CHCl₃ / CH₂Cl₂ / 20 °C

3: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation

4: Cs₂CO₃; Bu₄NI / dimethylformamide / 2 h

5: 8.7 mg / pyridine / 3 h / 20 °C

6: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C

7: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

8: 6.5 mg / NaBH₄ / CH₂Cl₂; methanol / 0.5 h / -78 °C

With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); sodium tetrahydroborate; sodium periodate; AD-mix-α; dimethylsulfide; methanesulfonamide; tetra-(n-butyl)ammonium iodide; caesium carbonate; magnesium bromide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Claisen rearrangement / 6: Sharpless asymmetric dihydroxylation;

DOI:10.1021/ja070571s

upstream raw materials:

8-benzenesulfonyl-2,6-dimethyl-octa-1,6-dien-3-ol

[3-(5-benzenesulfonyl-3-methyl-pent-3-enyl)-2-methyl-oxiranyl]-methanol

5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-3-ene-1,2-dione

4-allyl-5-(4-hydroxy-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

Downstream raw materials:

7-hydroxy-3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(?)-terpestacin