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

Base Information

• Chemical Name: (E)-(R)-4-[(1R,2S)-2-((E)-(R)-6-Hydroxy-hept-1-enyl)-cyclopentyl]-4-(4-methoxy-benzyloxy)-but-2-enoic acid methyl ester
• CAS No.: 135330-05-1
• Molecular Formula: C₂₅H₃₆O₅
• Molecular Weight: 416.558
• Mol file: 135330-05-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about (E)-(R)-4-[(1R,2S)-2-((E)-(R)-6-Hydroxy-hept-1-enyl)-cyclopentyl]-4-(4-methoxy-benzyloxy)-but-2-enoic acid methyl 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:

tetrahydro-2H-2-pyranol (694-54-2) → (E)-(R)-4-[(1R,2S)-2-((E)-(R)-6-Hydroxy-hept-1-enyl)-cyclopentyl]-4-(4-methoxy-benzyloxy)-but-2-enoic acid methyl ester (135330-05-1)

Guidance literature:

Multi-step reaction with 18 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

With 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; carbon tetrabromide; 4 A molecular sieve; potassium tert-butylate; ammonia; sodium methylate; tin(IV) chloride; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ozone; triethylamine; triphenylphosphine; 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) → (E)-(R)-4-[(1R,2S)-2-((E)-(R)-6-Hydroxy-hept-1-enyl)-cyclopentyl]-4-(4-methoxy-benzyloxy)-but-2-enoic acid methyl ester (135330-05-1)

Guidance literature:

Multi-step reaction with 17 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

With 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; carbon tetrabromide; 4 A molecular sieve; potassium tert-butylate; ammonia; sodium methylate; tin(IV) chloride; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ozone; triethylamine; triphenylphosphine; 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:

E,Z-trimethylsilylhept-5-en-1-al (92121-09-0,92121-12-5,119554-50-6) → (E)-(R)-4-[(1R,2S)-2-((E)-(R)-6-Hydroxy-hept-1-enyl)-cyclopentyl]-4-(4-methoxy-benzyloxy)-but-2-enoic acid methyl ester (135330-05-1)

Guidance literature:

Multi-step reaction with 16 steps

1: t-BuOK / tetrahydrofuran / -78 °C

2: DIBAL / CH₂Cl₂ / -78 °C

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

4: 82 percent / Sncl₄ / CH₂Cl₂ / -90 °C

5: CSA / acetone

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

7: Ph₃P, CBr₄ / CH₂Cl₂ / 0 °C

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

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

10: MeOH / p-TsOH

11: CSA

12: imidazole / dimethylformamide

13: DIBAL / toluene

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

15: t-BuOK / tetrahydrofuran / -78 °C

16: p-TsOH / methanol

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

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

upstream raw materials:

tetrahydro-2H-2-pyranol

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

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

(S)-1-((R)-2-Vinyl-cyclopentyl)-ethane-1,2-diol

Downstream raw materials:

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

(+)-brefeldin C

(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