(5E,13E)-(3aR,4R,9S,14aS)-4-(4-Methoxy-benzyloxy)-9-methyl-2,3,3a,9,10,11,12,14a-octahydro-1H,4H-8-oxa-cyclopentacyclotridecen-7-one

Base Information

• Chemical Name: (5E,13E)-(3aR,4R,9S,14aS)-4-(4-Methoxy-benzyloxy)-9-methyl-2,3,3a,9,10,11,12,14a-octahydro-1H,4H-8-oxa-cyclopentacyclotridecen-7-one
• CAS No.: 126761-02-2
• Molecular Formula: C₂₄H₃₂O₄
• Molecular Weight: 384.516
• Mol file: 126761-02-2.mol

Synonyms:

Chemical Property of (5E,13E)-(3aR,4R,9S,14aS)-4-(4-Methoxy-benzyloxy)-9-methyl-2,3,3a,9,10,11,12,14a-octahydro-1H,4H-8-oxa-cyclopentacyclotridecen-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5E,13E)-(3aR,4R,9S,14aS)-4-(4-Methoxy-benzyloxy)-9-methyl-2,3,3a,9,10,11,12,14a-octahydro-1H,4H-8-oxa-cyclopentacyclotridecen-7-one

There total 19 articles about (5E,13E)-(3aR,4R,9S,14aS)-4-(4-Methoxy-benzyloxy)-9-methyl-2,3,3a,9,10,11,12,14a-octahydro-1H,4H-8-oxa-cyclopentacyclotridecen-7-one 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:

(E)-(R)-4-[(1R,2S)-2-((E)-(R)-6-Hydroxy-hept-1-enyl)-cyclopentyl]-4-(4-methoxy-benzyloxy)-but-2-enoic acid (126761-01-1) → (5E,13E)-(3aR,4R,9S,14aS)-4-(4-Methoxy-benzyloxy)-9-methyl-2,3,3a,9,10,11,12,14a-octahydro-1H,4H-8-oxa-cyclopentacyclotridecen-7-one (126761-02-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 ℃; Yield given;

DOI:10.1016/S0040-4039(01)80524-4

Reference yield:

tetrahydro-2H-2-pyranol (694-54-2) → (5E,13E)-(3aR,4R,9S,14aS)-4-(4-Methoxy-benzyloxy)-9-methyl-2,3,3a,9,10,11,12,14a-octahydro-1H,4H-8-oxa-cyclopentacyclotridecen-7-one (126761-02-2)

Guidance literature:

Multi-step reaction with 20 steps

2: (COCl)2, Et₃N / dimethylsulfoxide / -50 - 0 °C

3: t-BuOK / tetrahydrofuran / -78 °C

4: DIBAL / CH₂Cl₂ / -78 °C

5: Ti(OiPr)4, D-(-)DIPT, t-BuOOH, 4A molecular sieves / CH₂Cl₂ / -25 °C

6: 82 percent / Sncl₄ / CH₂Cl₂ / -90 °C

7: CSA / acetone

8: 1.) O₃, NaHCO₃; 2.) NaOMe / 1.) CH₂Cl/MeOH, -78 deg C; 2.) MeOH

9: Ph₃P, CBr₄ / CH₂Cl₂ / 0 °C

10: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) HMPA, from -78 to 0 deg C

11: Li, NH₃ / 2-methyl-propan-2-ol / -33 °C

12: MeOH / p-TsOH

13: CSA

14: imidazole / dimethylformamide

15: DIBAL / toluene

16: (COCl)2, Et₃N / CH₂Cl₂ / -50 - 0 °C

17: t-BuOK / tetrahydrofuran / -78 °C

18: p-TsOH / methanol

19: LiOH/H₂O / methanol

20: DEAD, Ph₃P / toluene / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; lithium hydroxide; n-butyllithium; oxalyl dichloride; carbon tetrabromide; 4 A molecular sieve; potassium tert-butylate; ammonia; water; sodium methylate; tin(IV) chloride; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ozone; triethylamine; triphenylphosphine; diethylazodicarboxylate; camphor-10-sulfonic acid; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(01)80524-4

Reference yield:

7-(trimethylsilyl)-(E,Z)-5-hepten-1-ol (119554-49-3) → (5E,13E)-(3aR,4R,9S,14aS)-4-(4-Methoxy-benzyloxy)-9-methyl-2,3,3a,9,10,11,12,14a-octahydro-1H,4H-8-oxa-cyclopentacyclotridecen-7-one (126761-02-2)

Guidance literature:

Multi-step reaction with 19 steps

1: (COCl)2, Et₃N / dimethylsulfoxide / -50 - 0 °C

2: t-BuOK / tetrahydrofuran / -78 °C

3: DIBAL / CH₂Cl₂ / -78 °C

4: Ti(OiPr)4, D-(-)DIPT, t-BuOOH, 4A molecular sieves / CH₂Cl₂ / -25 °C

5: 82 percent / Sncl₄ / CH₂Cl₂ / -90 °C

6: CSA / acetone

7: 1.) O₃, NaHCO₃; 2.) NaOMe / 1.) CH₂Cl/MeOH, -78 deg C; 2.) MeOH

8: Ph₃P, CBr₄ / CH₂Cl₂ / 0 °C

9: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) HMPA, from -78 to 0 deg C

10: Li, NH₃ / 2-methyl-propan-2-ol / -33 °C

11: MeOH / p-TsOH

12: CSA

13: imidazole / dimethylformamide

14: DIBAL / toluene

15: (COCl)2, Et₃N / CH₂Cl₂ / -50 - 0 °C

16: t-BuOK / tetrahydrofuran / -78 °C

17: p-TsOH / methanol

18: LiOH/H₂O / methanol

19: DEAD, Ph₃P / toluene / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; lithium hydroxide; n-butyllithium; oxalyl dichloride; carbon tetrabromide; 4 A molecular sieve; potassium tert-butylate; ammonia; water; sodium methylate; tin(IV) chloride; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ozone; triethylamine; triphenylphosphine; diethylazodicarboxylate; camphor-10-sulfonic acid; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(01)80524-4

upstream raw materials:

(E)-(R)-4-[(1R,2S)-2-((E)-(R)-6-Hydroxy-hept-1-enyl)-cyclopentyl]-4-(4-methoxy-benzyloxy)-but-2-enoic acid

tetrahydro-2H-2-pyranol

7-(trimethylsilyl)-(E,Z)-5-hepten-1-ol

E,Z-trimethylsilylhept-5-en-1-al

Downstream raw materials:

(+)-brefeldin C