O-benzyldihydromevinolin

Base Information

• Chemical Name: O-benzyldihydromevinolin
• CAS No.: 129264-92-2
• Molecular Formula: C₃₁H₄₄O₅
• Molecular Weight: 496.687
• Mol file: 129264-92-2.mol

Synonyms:O-benzyldihydromevinolin

Chemical Property of O-benzyldihydromevinolin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-benzyldihydromevinolin

There total 31 articles about O-benzyldihydromevinolin 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: 78.0%

(1S,2S,4aR,6S,8S,8aS)-1-<2-<2(R)-<4(R)-(benzyloxy)-1-oxocyclopentyl>>ethyl>-2,6-dimethyl-8-<<(S)-2-methyl-1-oxobutyl>oxy>-1,2,4a,5,6,7,8,8a-octahydronaphthalene (129264-91-1) → O-benzyldihydromevinolin (129264-92-2)

Guidance literature:

With bis-trimethylsilanyl peroxide; boron trifluoride diethyl etherate; In dichloromethane; for 1.5h; Ambient temperature; 2;

DOI:10.1021/jo00309a022

Reference yield:

(1R,2S,4aR,6S,8S,8aS)-1-carboxy-2,6-dimethoxy-8-hydroxy-1,2,4a,5,6,7,8,8a-octahydronaphthalene 1,8 lactone (129264-77-3) → O-benzyldihydromevinolin (129264-92-2)

Guidance literature:

Multi-step reaction with 18 steps

1: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C

2: 91 percent / pyridine / Ambient temperature

3: 85 percent / triethylamine / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C

5: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH₂Cl₂, -10 deg C, 20 min 2.) -10 deg C, 5 min

6: 53 percent / K₂CO₃ / methanol / 19 h / 100 °C

7: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature

8: 85 percent / methanesulfonyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 °C

9: 90 percent / NaBH₄ / propan-2-ol; CHCl₃ / 0.67 h / Ambient temperature

10: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature

11: 70 percent / DMAP / 0.33 h / 40 °C

12: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature

13: 55 percent / n-Bu₃SnH, AIBN / toluene / 0.5 h / Heating

14: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight

15: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature

16: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature

17: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 15 min 2.) -60 deg C, 15 min

18: 78 percent / BF_3.Et₂O, bis(trimethylsilyl)peroxide / CH₂Cl₂ / 1.5 h / Ambient temperature; 2

With pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; Amberlyst A-21; 2,2'-azobis(isobutyronitrile); bis-trimethylsilanyl peroxide; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1021/jo00309a022

Reference yield:

(1R,2S,4aR,6S,8S,8aS)-1-(acetoxymethyl)-2,6-dimethyl-8-hydroxy-1,2,4a,5,6,7,8,8a-octahydronaphthalene (129285-43-4) → O-benzyldihydromevinolin (129264-92-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 85 percent / triethylamine / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C

3: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH₂Cl₂, -10 deg C, 20 min 2.) -10 deg C, 5 min

4: 53 percent / K₂CO₃ / methanol / 19 h / 100 °C

5: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature

6: 85 percent / methanesulfonyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 °C

7: 90 percent / NaBH₄ / propan-2-ol; CHCl₃ / 0.67 h / Ambient temperature

8: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature

9: 70 percent / DMAP / 0.33 h / 40 °C

10: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature

11: 55 percent / n-Bu₃SnH, AIBN / toluene / 0.5 h / Heating

12: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight

13: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature

14: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature

15: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 15 min 2.) -60 deg C, 15 min

16: 78 percent / BF_3.Et₂O, bis(trimethylsilyl)peroxide / CH₂Cl₂ / 1.5 h / Ambient temperature; 2

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; Amberlyst A-21; 2,2'-azobis(isobutyronitrile); bis-trimethylsilanyl peroxide; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1021/jo00309a022

upstream raw materials:

(1S,2S,4aR,6S,8S,8aS)-1-<2-<2(R)-<4(R)-(benzyloxy)-1-oxocyclopentyl>>ethyl>-2,6-dimethyl-8-<<(S)-2-methyl-1-oxobutyl>oxy>-1,2,4a,5,6,7,8,8a-octahydronaphthalene

(1R,2S,4aR,6S,8S,8aS)-1-carboxy-2,6-dimethoxy-8-hydroxy-1,2,4a,5,6,7,8,8a-octahydronaphthalene 1,8 lactone

(2S,4R,5S,6E,8E)-5-(methoxymethoxy)-4-methyl-6,8-decadien-1,2-diol

(2S,4R,5S,6E,8E)-1,2-epoxy-5-(methoxymethoxy)-4-methyl-6,8-decadiene

Downstream raw materials:

(+)-Dihydromevinolin