(3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

Base Information

Chemical Name:(3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
CAS No.:1449374-90-6
Molecular Formula:C₂₉H₄₀O₅Si
Molecular Weight:496.719
Hs Code.:

Synonyms:(3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

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Chemical Property of (3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

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Technology Process of (3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

There total 5 articles about (3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-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:

: 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

: 77-76-9
2,2-dimethoxy-propane

: 1449374-90-6
(3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 0 - 20 ℃; for 4h;
DOI:10.1016/j.tet.2013.05.067

Reference yield:

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

: 1449374-90-6
(3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

Guidance literature:: Multi-step reaction with 5 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

5: toluene-4-sulfonic acid / acetone / 4 h / 0 - 20 °C

With 1H-imidazole; methanol; iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; hydrogen bromide; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2013.05.067

Reference yield:

: 13242-53-0
acetobromomannose

: 1449374-90-6
(3aR,4R,6R,7R,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4-(2-methyl-prop-1-en-1-yl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

Guidance literature:: Multi-step reaction with 4 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

4: toluene-4-sulfonic acid / acetone / 4 h / 0 - 20 °C

With 1H-imidazole; methanol; iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2013.05.067