{(1S,2S,4aR,5R)-5-benzenesulfonylmethyl-2,5-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ylmethoxy}-tert-butyldimethylsilane

Base Information

Chemical Name:{(1S,2S,4aR,5R)-5-benzenesulfonylmethyl-2,5-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ylmethoxy}-tert-butyldimethylsilane
CAS No.:535932-74-2
Molecular Formula:C₃₃H₅₄O₅SSi
Molecular Weight:590.94
Hs Code.:

{(1S,2S,4aR,5R)-5-benzenesulfonylmethyl-2,5-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ylmethoxy}-tert-butyldimethylsilane

Synonyms:{(1S,2S,4aR,5R)-5-benzenesulfonylmethyl-2,5-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ylmethoxy}-tert-butyldimethylsilane

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Chemical Property of {(1S,2S,4aR,5R)-5-benzenesulfonylmethyl-2,5-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ylmethoxy}-tert-butyldimethylsilane

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Technology Process of {(1S,2S,4aR,5R)-5-benzenesulfonylmethyl-2,5-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ylmethoxy}-tert-butyldimethylsilane

There total 13 articles about {(1S,2S,4aR,5R)-5-benzenesulfonylmethyl-2,5-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ylmethoxy}-tert-butyldimethylsilane 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: 95.0%

: 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

: 535932-74-2
{(1S,2S,4aR,5R)-5-benzenesulfonylmethyl-2,5-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ylmethoxy}-tert-butyldimethylsilane

Guidance literature:: With molecular sieve; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 31h;
DOI:10.1021/jo020743y

Reference yield:

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

: 535932-74-2
{(1S,2S,4aR,5R)-5-benzenesulfonylmethyl-2,5-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ylmethoxy}-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 7 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

7.1: 95 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; molecular sieves / CH₂Cl₂ / 31 h / 20 °C

With pyridine; 1H-imidazole; lithium borohydride; n-butyllithium; thionyl chloride; molecular sieve; tetrapropylammonium perruthennate; tributylphosphine; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 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

: 535932-74-2
{(1S,2S,4aR,5R)-5-benzenesulfonylmethyl-2,5-dimethyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ylmethoxy}-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 11 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

11.1: 95 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; molecular sieves / CH₂Cl₂ / 31 h / 20 °C

With pyridine; 1H-imidazole; dmap; platinum(IV) oxide; lithium borohydride; n-butyllithium; thionyl chloride; molecular sieve; tetrapropylammonium perruthennate; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; diisopropylamine; dicyclohexyl-carbodiimide; propynoic acid ethyl ester; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene; 2.1: intramolecular Diels-Alder reaction;
DOI:10.1021/jo020743y