(2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

Chemical Name:(2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol
CAS No.:1449374-89-3
Molecular Formula:C₂₆H₃₆O₅Si
Molecular Weight:456.654
Hs Code.:

Synonyms:(2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

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Chemical Property of (2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

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Technology Process of (2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

There total 4 articles about (2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol 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:

: 1449374-88-2
(2R,3S,4R,5S,6R)-2-(hydroxymethyl)-6-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran-3,4,5-triol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1449374-89-3
(2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 5h;
DOI:10.1016/j.tet.2013.05.067

Reference yield:

: 4163-65-9
per-O-acetyl-α-D-mannopyranose

: 1449374-89-3
(2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 4 steps

1: hydrogen bromide / dichloromethane; acetic acid / 0 - 20 °C

2: iron(III) chloride; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 20 °C

3: potassium carbonate; methanol / 20 °C

4: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 0 - 20 °C

With 1H-imidazole; methanol; iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; hydrogen bromide; potassium carbonate; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2013.05.067

Reference yield:

: 13242-53-0
acetobromomannose

: 1449374-89-3
(2R,3S,4R,5S,6R)-2-(2-methylprop-1-en-1-yl)-6-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 3 steps

1: iron(III) chloride; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 20 °C

2: potassium carbonate; methanol / 20 °C

3: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 0 - 20 °C

With 1H-imidazole; methanol; iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2013.05.067