(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

Base Information

Chemical Name:(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
CAS No.:535932-87-7
Molecular Formula:C₃₃H₅₆O₄SSi
Molecular Weight:576.957
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 11 articles about (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 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: 92.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 535932-86-6
(1R,4R,4aR,7S,8S,8aR)-8-Hydroxymethyl-4,7-dimethyl-4-phenylsulfanylmethyl-8-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-decahydro-naphthalen-1-ol

: 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

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1021/jo020743y

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 5 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

With pyridine; 1H-imidazole; lithium borohydride; n-butyllithium; 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

: 535932-87-7
(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

Guidance literature:: Multi-step reaction with 9 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

With pyridine; 1H-imidazole; dmap; platinum(IV) oxide; lithium borohydride; n-butyllithium; 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