tert-Butyl-{(1S,2S,4aR,5R)-2,5-dimethyl-5-phenylsulfanylmethyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethoxy}-dimethyl-silane

Base Information

Chemical Name:tert-Butyl-{(1S,2S,4aR,5R)-2,5-dimethyl-5-phenylsulfanylmethyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethoxy}-dimethyl-silane
CAS No.:535932-88-8
Molecular Formula:C₃₃H₅₄O₃SSi
Molecular Weight:558.941
Hs Code.:

tert-Butyl-{(1S,2S,4aR,5R)-2,5-dimethyl-5-phenylsulfanylmethyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethoxy}-dimethyl-silane

Synonyms:tert-Butyl-{(1S,2S,4aR,5R)-2,5-dimethyl-5-phenylsulfanylmethyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethoxy}-dimethyl-silane

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Chemical Property of tert-Butyl-{(1S,2S,4aR,5R)-2,5-dimethyl-5-phenylsulfanylmethyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethoxy}-dimethyl-silane

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Technology Process of tert-Butyl-{(1S,2S,4aR,5R)-2,5-dimethyl-5-phenylsulfanylmethyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethoxy}-dimethyl-silane

There total 12 articles about tert-Butyl-{(1S,2S,4aR,5R)-2,5-dimethyl-5-phenylsulfanylmethyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethoxy}-dimethyl-silane 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: 97.0%

: 535932-87-7
(1R,4R,4aR,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-4,7-dimethyl-4-phenylsulfanylmethyl-8-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-decahydro-naphthalen-1-ol

: 535932-88-8
tert-Butyl-{(1S,2S,4aR,5R)-2,5-dimethyl-5-phenylsulfanylmethyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethoxy}-dimethyl-silane

Guidance literature:: With pyridine; thionyl chloride; at 0 ℃; for 0.75h;
DOI:10.1021/jo020743y

Reference yield:

: 14204-24-1
N-(phenylthio)succinimide

: 535932-88-8
tert-Butyl-{(1S,2S,4aR,5R)-2,5-dimethyl-5-phenylsulfanylmethyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethoxy}-dimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 79 percent / Bu₃P; pyridine / 1.5 h / 60 °C

2.1: BuLi; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / 0 °C

2.2: 97 percent / HMPA / hexane; tetrahydrofuran / 2 h / 0 °C

3.1: DIBALH / hexane; toluene / 0.5 h / -78 °C

4.1: 413 mg / LiBH₄ / tetrahydrofuran / 19 h / 40 °C

5.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C

6.1: 97 percent / SOCl₂; pyridine / 0.75 h / 0 °C

With pyridine; 1H-imidazole; lithium borohydride; n-butyllithium; thionyl chloride; tributylphosphine; diisobutylaluminium hydride; diisopropylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo020743y

Reference yield:

: 331627-36-2
(1R,4R)-3-(2-Benzenesulfinyl-ethyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-cyclohex-2-enol

: 535932-88-8
tert-Butyl-{(1S,2S,4aR,5R)-2,5-dimethyl-5-phenylsulfanylmethyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethoxy}-dimethyl-silane

Guidance literature:: Multi-step reaction with 10 steps

1.1: 95 percent / DCC; DMAP / toluene / 0.5 h / 0 °C

2.1: 84 percent / ethyl propiolate; pyridine / toluene / 61 h / Heating

3.1: H₂; PtO₂ / acetic acid / 30 h / 20 °C / 3040 Torr

4.1: 369 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5.1: 79 percent / Bu₃P; pyridine / 1.5 h / 60 °C

6.1: BuLi; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / 0 °C

6.2: 97 percent / HMPA / hexane; tetrahydrofuran / 2 h / 0 °C

7.1: DIBALH / hexane; toluene / 0.5 h / -78 °C

8.1: 413 mg / LiBH₄ / tetrahydrofuran / 19 h / 40 °C

9.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C

10.1: 97 percent / SOCl₂; pyridine / 0.75 h / 0 °C

With pyridine; 1H-imidazole; dmap; platinum(IV) oxide; lithium borohydride; n-butyllithium; thionyl chloride; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; diisopropylamine; dicyclohexyl-carbodiimide; propynoic acid ethyl ester; In tetrahydrofuran; hexane; acetic acid; N,N-dimethyl-formamide; toluene; 2.1: intramolecular Diels-Alder reaction;
DOI:10.1021/jo020743y