(2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((R)-1-hydroxy-but-3-enyl)-3,6-dimethyl-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((R)-1-hydroxy-but-3-enyl)-3,6-dimethyl-tetrahydro-pyran-3-ol
CAS No.:176107-82-7
Molecular Formula:C₂₈H₄₀O₄Si
Molecular Weight:468.709
Hs Code.:

Synonyms:(2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((R)-1-hydroxy-but-3-enyl)-3,6-dimethyl-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((R)-1-hydroxy-but-3-enyl)-3,6-dimethyl-tetrahydro-pyran-3-ol

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Technology Process of (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((R)-1-hydroxy-but-3-enyl)-3,6-dimethyl-tetrahydro-pyran-3-ol

There total 6 articles about (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((R)-1-hydroxy-but-3-enyl)-3,6-dimethyl-tetrahydro-pyran-3-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: 54.0%

: 1826-67-1
vinyl magnesium bromide

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

: 176107-82-7
(2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((R)-1-hydroxy-but-3-enyl)-3,6-dimethyl-tetrahydro-pyran-3-ol

Guidance literature:: With copper(l) iodide; In tetrahydrofuran; at -23 ℃;
DOI:10.1248/cpb.44.627

Reference yield:

: 174198-74-4
(2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-3-ol

: 176107-82-7
(2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((R)-1-hydroxy-but-3-enyl)-3,6-dimethyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO, CH₂Cl₂, -78 deg C, 2.) DMSO, CH₂Cl₂, RT

2: 47 percent / CH₂Cl₂ / -20 °C

3: 83 percent / aq. AcOH / Ambient temperature

4: 94 percent / Et₃N / CH₂Cl₂ / 0 °C

5: 95 percent / K₂CO₃ / methanol / Ambient temperature

6: 54 percent / CuI / tetrahydrofuran / -23 °C

With copper(l) iodide; oxalyl dichloride; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1248/cpb.44.627

Reference yield:

: 1053734-22-7
(R)-1-[(2S,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-2,5-dimethyl-tetrahydro-pyran-2-yl]-ethane-1,2-diol

: 176107-82-7
(2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((R)-1-hydroxy-but-3-enyl)-3,6-dimethyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / Et₃N / CH₂Cl₂ / 0 °C

2: 95 percent / K₂CO₃ / methanol / Ambient temperature

3: 54 percent / CuI / tetrahydrofuran / -23 °C

With copper(l) iodide; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1248/cpb.44.627