acetic acid 3-(2,3-dihydroxy-1-methyl-butyl)-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-(2,3-dihydroxy-1-methyl-butyl)-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.: 935263-68-6
• Molecular Formula: C₃₇H₅₂O₇
• Molecular Weight: 608.816
• Mol file: 935263-68-6.mol

Synonyms:acetic acid 3-(2,3-dihydroxy-1-methyl-butyl)-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-(2,3-dihydroxy-1-methyl-butyl)-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-(2,3-dihydroxy-1-methyl-butyl)-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 16 articles about acetic acid 3-(2,3-dihydroxy-1-methyl-butyl)-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: 65.0%

acetic acid 2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-3-(1-methyl-but-2-enyl)-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester (935263-67-5) → acetic acid 3-(2,3-dihydroxy-1-methyl-butyl)-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 (935263-68-6)

Guidance literature:

With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 4 ℃; for 48h;

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-(2,3-dihydroxy-1-methyl-butyl)-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 (935263-68-6)

Guidance literature:

Multi-step reaction with 10 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

With N,N,N,N,N,N-hexamethylphosphoric triamide; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); sodium tetrahydroborate; 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; 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:

4-allyl-2-(4-methoxy-benzyloxy)-5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-2-enone (935263-70-0) → acetic acid 3-(2,3-dihydroxy-1-methyl-butyl)-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 (935263-68-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 84 percent / TBAF*3H₂O / tetrahydrofuran / 2 h / 0 °C

2: 88 percent / PPh₃; CBr₄ / acetonitrile / 20 °C

3: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C

4: 77 percent / NaBH₄; DPPP / Pd(OAc)2 / dimethylsulfoxide

5: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C

6: 93 percent / dimethyl sulfide; MgBr₂*Et₂O / CH₂Cl₂ / 0.67 h / 20 °C

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

8: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation

9: Cs₂CO₃; Bu₄NI / dimethylformamide / 2 h

10: 8.7 mg / pyridine / 3 h / 20 °C

11: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °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; AD-mix-α; dimethylsulfide; carbon tetrabromide; methanesulfonamide; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; 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; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 8: Claisen rearrangement / 11: Sharpless asymmetric dihydroxylation;

DOI:10.1021/ja070571s

upstream raw materials:

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

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

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

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

(?)-terpestacin