(3R,3aR,6R,7S,7aS)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-one

Base Information

• Chemical Name: (3R,3aR,6R,7S,7aS)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-one
• CAS No.: 263340-98-3
• Molecular Formula: C₂₇H₄₂O₃
• Molecular Weight: 414.629

Synonyms:(3R,3aR,6R,7S,7aS)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-one

Chemical Property of (3R,3aR,6R,7S,7aS)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aR,6R,7S,7aS)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-one

There total 19 articles about (3R,3aR,6R,7S,7aS)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-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: 67.0%

2,2-Dimethyl-propionic acid 2-[(1R,3aS,4S,5R,7aR)-5-benzyloxy-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-3-oxo-octahydro-inden-4-yl]-ethyl ester (263340-94-9) → (3R,3aR,6R,7S,7aR)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-one (263340-96-1) + (3R,3aR,6R,7S,7aS)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-one (263340-98-3)

Guidance literature:

sodium methylate; In methanol; for 2h;

DOI:10.1002/(SICI)1099-0690(200002)2000:3<439::AID-EJOC439>3.0.CO;2-F

Reference yield:

Grundmann's ketone (66251-18-1) → (3R,3aR,6R,7S,7aS)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-one (263340-98-3)

Guidance literature:

Multi-step reaction with 19 steps

1.1: LiI; HN(TMS)2 / CH₂Cl₂ / 3 h

2.1: 84 percent / tetrahydrofuran; pyridine / 0.5 h / -78 °C

3.1: 83 percent / MCPBA / CH₂Cl₂ / 0.5 h

4.1: 80 percent / NaBH₄; CeCl₃*7H₂O / methanol / 1 h

5.1: 90 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 3 h / Heating

6.1: BH₃*SMe₂ / tetrahydrofuran / 3 h / 20 °C

6.2: 62 percent / H₂O₂; NaOH / ethanol; H₂O / 1 h / Heating

7.1: 91 percent / iPr₂EtN / CH₂Cl₂ / 3 h / 20 °C

8.1: 100 percent / H₂ / Pd/C / ethanol / 1.5 h

9.1: 97 percent / PDC; 4-Angstroem molecular sieves / CH₂Cl₂ / 2 h

10.1: 90 percent / LiN(TMS)2 / tetrahydrofuran / 2 h / 20 °C

11.1: 80 percent / LiCl / Pd(PPh₃)4 / tetrahydrofuran / 4 h / Heating

12.1: 87 percent / O₂; 5,10,15,20-tetraphenyl-21H,23H-porphine / CH₂Cl₂ / 2 h / -78 °C / Irradiation

13.1: 100 percent / NaNO₂; H₂ / PtO₂ / ethanol / 3 h

14.1: 86 percent / H₂; NaNO₂ / Pt/C / ethyl acetate / 2 h

15.1: 79 percent / pyridine; DMAP / CH₂Cl₂ / 1.5 h

16.1: 62 percent / NaH; TBAI / tetrahydrofuran / 2 h / Heating

17.1: 82 percent / TFA / CH₂Cl₂

18.1: 79 percent / PDC; 4-Angstroem molecular sieves / CH₂Cl₂ / 2 h

19.1: 67 percent / MeONa / methanol / 2 h

With pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; oxygen; 5,15,10,20-tetraphenylporphyrin; tetra-(n-butyl)ammonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; lithium chloride; lithium iodide; lithium hexamethyldisilazane; sodium nitrite; platinum(IV) oxide; palladium on activated charcoal; platinum on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium methylate; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; ethyl acetate; 1.1: Silylation / 2.1: Selenenylation / 3.1: Elimination / 4.1: Reduction / 5.1: Etherification / 6.1: Hydroboration / 6.2: Oxidation / 7.1: Etherification / 8.1: Hydrogenolysis / 9.1: Oxidation / 10.1: Substitution / 11.1: Vinylation; Stille coupling / 12.1: Cycloaddition / 13.1: Adam's reduction / 14.1: Hydrogenation / 15.1: Acylation / 16.1: Benzylation / 17.1: MEM-deprotection / 18.1: Oxidation / 19.1: Isomerization;

DOI:10.1002/(SICI)1099-0690(200002)2000:3<439::AID-EJOC439>3.0.CO;2-F

Reference yield:

De-A,B-cholest-14-en-8-one (93922-90-8) → (3R,3aR,6R,7S,7aS)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-one (263340-98-3)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 80 percent / NaBH₄; CeCl₃*7H₂O / methanol / 1 h

2.1: 90 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 3 h / Heating

3.1: BH₃*SMe₂ / tetrahydrofuran / 3 h / 20 °C

3.2: 62 percent / H₂O₂; NaOH / ethanol; H₂O / 1 h / Heating

4.1: 91 percent / iPr₂EtN / CH₂Cl₂ / 3 h / 20 °C

5.1: 100 percent / H₂ / Pd/C / ethanol / 1.5 h

6.1: 97 percent / PDC; 4-Angstroem molecular sieves / CH₂Cl₂ / 2 h

7.1: 90 percent / LiN(TMS)2 / tetrahydrofuran / 2 h / 20 °C

8.1: 80 percent / LiCl / Pd(PPh₃)4 / tetrahydrofuran / 4 h / Heating

9.1: 87 percent / O₂; 5,10,15,20-tetraphenyl-21H,23H-porphine / CH₂Cl₂ / 2 h / -78 °C / Irradiation

10.1: 100 percent / NaNO₂; H₂ / PtO₂ / ethanol / 3 h

11.1: 86 percent / H₂; NaNO₂ / Pt/C / ethyl acetate / 2 h

12.1: 79 percent / pyridine; DMAP / CH₂Cl₂ / 1.5 h

13.1: 62 percent / NaH; TBAI / tetrahydrofuran / 2 h / Heating

14.1: 82 percent / TFA / CH₂Cl₂

15.1: 79 percent / PDC; 4-Angstroem molecular sieves / CH₂Cl₂ / 2 h

16.1: 67 percent / MeONa / methanol / 2 h

With pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; oxygen; 5,15,10,20-tetraphenylporphyrin; tetra-(n-butyl)ammonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium chloride; lithium hexamethyldisilazane; sodium nitrite; platinum(IV) oxide; palladium on activated charcoal; platinum on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium methylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; 1.1: Reduction / 2.1: Etherification / 3.1: Hydroboration / 3.2: Oxidation / 4.1: Etherification / 5.1: Hydrogenolysis / 6.1: Oxidation / 7.1: Substitution / 8.1: Vinylation; Stille coupling / 9.1: Cycloaddition / 10.1: Adam's reduction / 11.1: Hydrogenation / 12.1: Acylation / 13.1: Benzylation / 14.1: MEM-deprotection / 15.1: Oxidation / 16.1: Isomerization;

DOI:10.1002/(SICI)1099-0690(200002)2000:3<439::AID-EJOC439>3.0.CO;2-F

upstream raw materials:

2,2-Dimethyl-propionic acid 2-[(1R,3aS,4S,5R,7aR)-5-benzyloxy-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-3-oxo-octahydro-inden-4-yl]-ethyl ester

Grundmann's ketone

De-A,B-cholest-14-en-8-one

(8R)-De-A,B-cholest-14-en-8-ol

Downstream raw materials:

(3R,3aR,6R,7S,7aR)-6-Benzyloxy-3-((R)-1,5-dimethyl-hexyl)-7-(2-hydroxy-ethyl)-3a-methyl-octahydro-inden-1-one

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