(2S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-ol

Base Information

Chemical Name:(2S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-ol
CAS No.:913722-20-0
Molecular Formula:C₂₅H₃₆O₄Si
Molecular Weight:428.644
Hs Code.:

Synonyms:(2S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-ol

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Chemical Property of (2S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-ol

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Technology Process of (2S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-ol

There total 5 articles about (2S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-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: 84.0%

: 913722-19-7
(2S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-one

: 913722-20-0
(2S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-ol

: (2S,4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-ol

Guidance literature:: With trimethylaluminum; isopropyl alcohol; In hexane; at 20 ℃; for 24h;
DOI:10.1021/ol061626i

Reference yield:

: 121467-56-9
(2R,4aR,6S,8aR)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

: 913722-20-0
(2S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / H₂ / Pd(OH)2/C / methanol / 24 h / 20 °C / 760 Torr

2: 91 percent / imidazole / dimethylformamide / 2 h / 20 °C

3: 83 percent / acetonitrile / 22 h / 20 °C

4: 95 percent / Bu₃SnH; AIBN / toluene / 0.83 h / 90 °C

5: 84 percent / Me₃Al; i-PrOH / hexane / 24 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); hydrogen; trimethylaluminum; tri-n-butyl-tin hydride; isopropyl alcohol; palladium dihydroxide; In methanol; hexane; N,N-dimethyl-formamide; toluene; acetonitrile; 4: Barton deoxygenation / 5: Meerwein-Ponndorf-Verley reduction;
DOI:10.1021/ol061626i

Reference yield:

: 913722-16-4
(2S,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-one

: 913722-20-0
(2S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / imidazole / dimethylformamide / 2 h / 20 °C

2: 83 percent / acetonitrile / 22 h / 20 °C

3: 95 percent / Bu₃SnH; AIBN / toluene / 0.83 h / 90 °C

4: 84 percent / Me₃Al; i-PrOH / hexane / 24 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); trimethylaluminum; tri-n-butyl-tin hydride; isopropyl alcohol; In hexane; N,N-dimethyl-formamide; toluene; acetonitrile; 3: Barton deoxygenation / 4: Meerwein-Ponndorf-Verley reduction;
DOI:10.1021/ol061626i