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

Base Information

Chemical Name:(E)-3-((3aS,4R,6S,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl)prop-2-en-1-ol
CAS No.:1449374-94-0
Molecular Formula:C₂₈H₃₈O₅Si
Molecular Weight:482.692
Hs Code.:

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

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

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

There total 10 articles about (E)-3-((3aS,4R,6S,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl)prop-2-en-1-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: 83.0%

: 1449374-93-9
(E)-ethyl 3-((3aS,4R,6S,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl)acrylate

: 1449374-94-0
(E)-3-((3aS,4R,6S,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl)prop-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; toluene; at -78 - 0 ℃;
DOI:10.1016/j.tet.2013.05.067

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

: 1449374-94-0
(E)-3-((3aS,4R,6S,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl)prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

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

2.1: 1H-imidazole; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C

2.2: 0.5 h / 20 °C

2.3: 0.17 h

3.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 2.5 h / 60 °C / Reflux

4.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol / 20 °C / pH 7

4.2: 3407 / 4 h / 20 °C / pH 7

5.1: dichloromethane / 1 h / 20 °C

6.1: diisobutylaluminium hydride / toluene; hexane / -78 - 0 °C

With 1H-imidazole; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene; mineral oil; tert-butyl alcohol; benzene; 3.1: |Barton-McCombie Deoxygenation;
DOI:10.1016/j.tet.2013.05.067

Reference yield:

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

: 1449374-94-0
(E)-3-((3aS,4R,6S,7aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl)prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 10 steps

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

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

3.1: potassium carbonate; methanol / 20 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 0 - 20 °C

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

6.1: 1H-imidazole; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C

6.2: 0.5 h / 20 °C

6.3: 0.17 h

7.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 2.5 h / 60 °C / Reflux

8.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol / 20 °C / pH 7

8.2: 3407 / 4 h / 20 °C / pH 7

9.1: dichloromethane / 1 h / 20 °C

10.1: diisobutylaluminium hydride / toluene; hexane / -78 - 0 °C

With 1H-imidazole; methanol; iron(III) chloride; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; hydrogen bromide; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol; benzene; 7.1: |Barton-McCombie Deoxygenation;
DOI:10.1016/j.tet.2013.05.067