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

Base Information

• Chemical Name: (1S,2S,4aR,6S,8S,8aS)-1-<2-<2(R)-<1(R)-hydroxy-4(R)-(benzyloxy)cyclopentyl>>ethyl>-2,6-dimethyl-8-<<(S)-2-methyl-1-oxobutyl>oxy>-1,2,4a,5,6,7,8,8a-octahydronaphthalene
• CAS No.: 129264-90-0
• Molecular Formula: C₃₁H₄₆O₄
• Molecular Weight: 482.704
• Mol file: 129264-90-0.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 29 articles about (1S,2S,4aR,6S,8S,8aS)-1-<2-<2(R)-<1(R)-hydroxy-4(R)-(benzyloxy)cyclopentyl>>ethyl>-2,6-dimethyl-8-<<(S)-2-methyl-1-oxobutyl>oxy>-1,2,4a,5,6,7,8,8a-octahydronaphthalene 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:

(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) → (1S,2S,4aR,6S,8S,8aS)-1-<2-<2(R)-<1(R)-hydroxy-4(R)-(benzyloxy)cyclopentyl>>ethyl>-2,6-dimethyl-8-<<(S)-2-methyl-1-oxobutyl>oxy>-1,2,4a,5,6,7,8,8a-octahydronaphthalene (129264-90-0)

Guidance literature:

Multi-step reaction with 14 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

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; Amberlyst A-21; 2,2'-azobis(isobutyronitrile); 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:

(1S,2S,4aR,6S,8S,8aS)-1-(nitroethyl)-2,6-dimethyl-8-hydroxy-1,2,4a,5,6,7,8,8a-octahydronaphthalene (129264-84-2) → (1S,2S,4aR,6S,8S,8aS)-1-<2-<2(R)-<1(R)-hydroxy-4(R)-(benzyloxy)cyclopentyl>>ethyl>-2,6-dimethyl-8-<<(S)-2-methyl-1-oxobutyl>oxy>-1,2,4a,5,6,7,8,8a-octahydronaphthalene (129264-90-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / DMAP / 0.33 h / 40 °C

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

3: 55 percent / n-Bu₃SnH, AIBN / toluene / 0.5 h / Heating

4: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight

5: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature

6: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature

With dmap; sodium tetrahydroborate; Amberlyst A-21; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1021/jo00309a022

Reference yield:

(2S,4R,5S,6E,8E)-5-(methoxymethoxy)-4-methyl-6,8-decadien-1,2-diol (129264-71-7) → (1S,2S,4aR,6S,8S,8aS)-1-<2-<2(R)-<1(R)-hydroxy-4(R)-(benzyloxy)cyclopentyl>>ethyl>-2,6-dimethyl-8-<<(S)-2-methyl-1-oxobutyl>oxy>-1,2,4a,5,6,7,8,8a-octahydronaphthalene (129264-90-0)

Guidance literature:

Multi-step reaction with 23 steps

1: 75 percent / pyridine / CH₂Cl₂ / -5 °C

2: 87 percent / sodium methoxide / CH₂Cl₂; methanol / 0.67 h / 0 °C

4: 65 percent / 2,6-di-tert-butyl-4-methylphenol / o-xylene / 144 h / Heating

5: 95 percent / 6 M HCl / tetrahydrofuran / 19 h / 40 °C

7: 68 percent / n-Bu₃SnH, AIBN / toluene / 0.58 h / Heating

8: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C

9: 91 percent / pyridine / Ambient temperature

10: 85 percent / triethylamine / CH₂Cl₂ / 0.5 h / Ambient temperature

11: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C

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

13: 53 percent / K₂CO₃ / methanol / 19 h / 100 °C

14: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature

15: 85 percent / methanesulfonyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 °C

16: 90 percent / NaBH₄ / propan-2-ol; CHCl₃ / 0.67 h / Ambient temperature

17: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature

18: 70 percent / DMAP / 0.33 h / 40 °C

19: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature

20: 55 percent / n-Bu₃SnH, AIBN / toluene / 0.5 h / Heating

21: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight

22: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature

23: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; Amberlyst A-21; 2,2'-azobis(isobutyronitrile); 2,6-di-tert-butyl-4-methyl-phenol; 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; o-xylene; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1021/jo00309a022

upstream raw materials:

benzyl bromide

(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:

(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

O-benzyldihydromevinolin

(+)-Dihydromevinolin