S-tert-butyl (2S)-2-[(1S,5R,7aS)-5-hydroxy-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate

Base Information

• Chemical Name: S-tert-butyl (2S)-2-[(1S,5R,7aS)-5-hydroxy-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate
• CAS No.: 332950-58-0
• Molecular Formula: C₃₀H₄₄O₄S₂
• Molecular Weight: 532.809
• Mol file: 332950-58-0.mol

Synonyms:S-tert-butyl (2S)-2-[(1S,5R,7aS)-5-hydroxy-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate

Chemical Property of S-tert-butyl (2S)-2-[(1S,5R,7aS)-5-hydroxy-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-tert-butyl (2S)-2-[(1S,5R,7aS)-5-hydroxy-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate

There total 9 articles about S-tert-butyl (2S)-2-[(1S,5R,7aS)-5-hydroxy-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate 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: 66.0%

S-tert-butyl (2RS)-2-[(1RS,7aRS)-7a-methyl-5-oxo-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-4-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate → S-tert-butyl (2S)-2-[(1S,5R,7aS)-5-hydroxy-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate (332950-58-0)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; methanol; at -78 ℃; for 2h;

DOI:10.1002/ejoc.200300611

Reference yield: 66.0%

2-(7a-methyl-5-oxo-4-phenylsulfanyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-3-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-thiopropionic acid S-tert-butyl ester (332950-57-9) → S-tert-butyl (2S)-2-[(1S,5R,7aS)-5-hydroxy-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate (332950-58-0)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride;

DOI:10.1016/S0040-4039(01)00317-3

Reference yield:

S-tert-butyl 3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate (332950-54-6) → S-tert-butyl (2S)-2-[(1S,5R,7aS)-5-hydroxy-7a-methyl-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate (332950-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / LDA / tetrahydrofuran; hexane

2.1: TrSbCl₆ / CH₂Cl₂ / 2 h / -78 °C

2.2: 79 percent / KOH / methanol / 1 h / 20 °C

3.1: 66 percent / CeCl₃*7H₂O; NaBH₄ / methanol; tetrahydrofuran / 2 h / -78 °C

With sodium tetrahydroborate; cerium(III) chloride; lithium diisopropyl amide; triphenylmethylium hexachloroantimonate(V); In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1002/ejoc.200300611

upstream raw materials:

2-(7a-methyl-5-oxo-4-phenylsulfanyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-3-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-thiopropionic acid S-tert-butyl ester

ethyl 5-methyl-4-hexenoate

(5S)-5-(1-hydroxy-1-methylethyl)dihydrofuran-2(3H)-one

S-tert-butyl 3-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]propanethioate

Downstream raw materials:

methyl (2E,5S)-5-[(1S,3aS,4S,7aS)-7a-methyl-4-(phenylsulfonyl)octahydro-1H-inden-1-yl]hex-2-enoate

[(S)-5-((1S,3aS,4S,7aS)-4-Benzenesulfonyl-7a-methyl-octahydro-inden-1-yl)-1,1-dimethyl-hexyloxy]-triethyl-silane

(1S,5R,7aS)-7a-methyl-4-phenylsulfonyl-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

(1S,5R,7aS)-7a-methyl-4-phenylthio-1-{(1S)-2-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-1-(tosyloxymethyl)ethyl}-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol