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

Base Information

• Chemical Name: 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
• CAS No.: 263340-94-9
• Molecular Formula: C₃₂H₅₀O₄
• Molecular Weight: 498.747

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 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

There total 18 articles about 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 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: 79.0%

2,2-Dimethyl-propionic acid 2-[(1R,3S,3aS,4S,5R,7aR)-5-benzyloxy-1-((R)-1,5-dimethyl-hexyl)-3-hydroxy-7a-methyl-octahydro-inden-4-yl]-ethyl ester (263340-92-7) → 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)

Guidance literature:

With dipyridinium dichromate; 4 A molecular sieve; In dichloromethane; 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) → 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)

Guidance literature:

Multi-step reaction with 18 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

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⁾; 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;

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) → 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)

Guidance literature:

Multi-step reaction with 15 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

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⁾; 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;

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,3S,3aS,4S,5R,7aR)-5-benzyloxy-1-((R)-1,5-dimethyl-hexyl)-3-hydroxy-7a-methyl-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

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

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