(1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol

Base Information

Chemical Name:(1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol
CAS No.:870862-60-5
Molecular Formula:C₂₆H₅₈O₅Si₃
Molecular Weight:535
Hs Code.:

Synonyms:(1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol

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Chemical Property of (1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol

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Technology Process of (1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol

There total 14 articles about (1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol 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%

: 870862-59-2
(1S,2S,3R,4R)-1-hydroxymethyl-3-methoxycyclohexan-1,2,4-triol

: 994-30-9
triethylsilyl chloride

: 870862-60-5
(1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 2h;
DOI:10.1021/jo051686m

Reference yield:

: 870862-48-9
(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol

: 870862-60-5
(1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / NaH / various solvent(s); tetrahydrofuran / 4 h / 0 °C

2: 72 percent / acetic acid / H₂O / 4.5 h / 50 °C

3: NaIO₄ / tetrahydrofuran; H₂O / 1.5 h / 20 °C

4: 3.04 g / tetrahydrofuran / 2 h / -20 °C

5: 84 percent / Grubbs' second generation catalyst / toluene / 1.5 h / 80 °C

6: 95 percent / H₂ / Pd/C / ethyl acetate / 21 h / 20 °C

7: 97 percent / HCl / methanol / 120 h / 0 - 20 °C

8: 95 percent / imidazole / dimethylformamide / 2 h / 0 °C

With 1H-imidazole; hydrogenchloride; sodium periodate; hydrogen; sodium hydride; acetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo051686m

Reference yield:

: 870862-51-4
(2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal

: 870862-60-5
(1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol

Guidance literature:: Multi-step reaction with 5 steps

1: 3.04 g / tetrahydrofuran / 2 h / -20 °C

2: 84 percent / Grubbs' second generation catalyst / toluene / 1.5 h / 80 °C

3: 95 percent / H₂ / Pd/C / ethyl acetate / 21 h / 20 °C

4: 97 percent / HCl / methanol / 120 h / 0 - 20 °C

5: 95 percent / imidazole / dimethylformamide / 2 h / 0 °C

With 1H-imidazole; hydrogenchloride; hydrogen; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo051686m