3-{(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-3-oxo-propionic acid allyl ester

Base Information

• Chemical Name: 3-{(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-3-oxo-propionic acid allyl ester
• CAS No.: 908255-78-7
• Molecular Formula: C₂₉H₄₀O₇
• Molecular Weight: 500.632
• Mol file: 908255-78-7.mol

Synonyms:3-{(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-3-oxo-propionic acid allyl ester

Chemical Property of 3-{(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-3-oxo-propionic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-3-oxo-propionic acid allyl ester

There total 15 articles about 3-{(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-3-oxo-propionic acid allyl 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%

3-Hydroxy-3-{(1R,3aR,7aR)-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-propionic acid allyl ester (908255-89-0) → 3-{(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-3-oxo-propionic acid allyl ester (908255-78-7)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo0608725

Reference yield:

(S)-2-((1R,7aR)-7a-Methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propan-1-ol (908255-69-6) → 3-{(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-3-oxo-propionic acid allyl ester (908255-78-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 74 percent / tetrabutylammonium iodide; NaH / tetrahydrofuran / 18 h / Heating

2: 0.308 g / m-chloroperoxybenzoic acid / CH₂Cl₂ / 2 h / -15 °C

3: 0.192 g / KOH / dimethylsulfoxide; H₂O / 18 h / 140 °C

4: triethylamine / tetrahydrofuran / 4 h / 20 °C

5: 4-(dimethylamino)pyridine; N,N-diisopropylethylamine / CH₂Cl₂ / 72 h / 20 °C

6: 1.17 g / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

7: 98 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 20 °C

8: 81 percent / LHMDS / tetrahydrofuran / 2 h / -45 °C

9: 87 percent / triethylamine; PdCl₂(PPh₃)2 / dimethylformamide / 18 h / 55 °C / 18100.2 Torr

10: 79 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

11: 98 percent / triethylamine; oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

12: 94 percent / LHMDS / tetrahydrofuran / 0.5 h / -78 °C

13: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 11: Swern oxidation;

DOI:10.1021/jo0608725

Reference yield:

Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester (64190-55-2) → 3-{(1R,3aR,7aR)-1-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-3-oxo-propionic acid allyl ester (908255-78-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 0.062 g / NaOH / methanol; H₂O / 18 h / 20 °C

2: 74 percent / tetrabutylammonium iodide; NaH / tetrahydrofuran / 18 h / Heating

3: 0.308 g / m-chloroperoxybenzoic acid / CH₂Cl₂ / 2 h / -15 °C

4: 0.192 g / KOH / dimethylsulfoxide; H₂O / 18 h / 140 °C

5: triethylamine / tetrahydrofuran / 4 h / 20 °C

6: 4-(dimethylamino)pyridine; N,N-diisopropylethylamine / CH₂Cl₂ / 72 h / 20 °C

7: 1.17 g / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

8: 98 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 20 °C

9: 81 percent / LHMDS / tetrahydrofuran / 2 h / -45 °C

10: 87 percent / triethylamine; PdCl₂(PPh₃)2 / dimethylformamide / 18 h / 55 °C / 18100.2 Torr

11: 79 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

12: 98 percent / triethylamine; oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

13: 94 percent / LHMDS / tetrahydrofuran / 0.5 h / -78 °C

14: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; sodium hydroxide; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 12: Swern oxidation;

DOI:10.1021/jo0608725

upstream raw materials:

3-Hydroxy-3-{(1R,3aR,7aR)-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-3a-methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}-propionic acid allyl ester

(S)-2-((1R,7aR)-7a-Methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propan-1-ol

Benzoic acid (S)-2-((1R,7aR)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-propyl ester

(3R,3aR)-3-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-3a-methyl-2,3,3a,4,5,6-hexahydro-1H-indene

Downstream raw materials:

C₄₄H₆₀O₅S₄Si

(1S,3S,5S,9R,10R,13R,17R)-3-(Dimethyl-phenyl-silanyl)-1-hydroxy-10-hydroxymethyl-17-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4,4,13-trimethyl-1,2,3,4,5,6,9,10,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-7-one

(3S,5S,9S,10R,13R,17R)-3-(Dimethyl-phenyl-silanyl)-17-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4,4,13-trimethyl-1,7-dioxo-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-10-carbaldehyde

(3S,5S,9S,10R,13R,17R)-3-(Dimethyl-phenyl-silanyl)-10-formyl-17-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4,4,13-trimethyl-1,7-dioxo-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-6-carboxylic acid allyl ester