((2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-6-methoxy-3-methylene-octahydro-pyrano[3,2-b]pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane

Base Information

Chemical Name:((2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-6-methoxy-3-methylene-octahydro-pyrano[3,2-b]pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane
CAS No.:328535-20-2
Molecular Formula:C₂₈H₄₄O₅Si
Molecular Weight:488.74
Hs Code.:

Synonyms:((2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-6-methoxy-3-methylene-octahydro-pyrano[3,2-b]pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane

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Chemical Property of ((2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-6-methoxy-3-methylene-octahydro-pyrano[3,2-b]pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane

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Technology Process of ((2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-6-methoxy-3-methylene-octahydro-pyrano[3,2-b]pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane

There total 5 articles about ((2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-6-methoxy-3-methylene-octahydro-pyrano[3,2-b]pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane 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:

: 194039-11-7
3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde

: 328535-20-2
((2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-6-methoxy-3-methylene-octahydro-pyrano[3,2-b]pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 0.58 h / Heating

1.2: 93 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: 1.91 g / oxalyl chloride; DMSO / CH₂Cl₂ / 1.5 h / -78 °C

3.1: camphorsulfonic acid / benzene / 7 h / Heating

4.1: 573 mg / Et₃N; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

5.1: 89 percent / DMSO; trifluoroacetic anhydride / CH₂Cl₂ / 1.5 h / -78 °C

6.1: potassium bis(trimethylsilyl)amide / toluene / 0.5 h / 80 - 90 °C

6.2: 84 percent / toluene / 0.5 h / 80 - 90 °C

With dmap; oxalyl dichloride; camphor-10-sulfonic acid; potassium hexamethylsilazane; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; toluene; benzene;
DOI:10.1021/jo001433n

Reference yield:

: (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-hydroxymethyl-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

: 328535-20-2
((2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-6-methoxy-3-methylene-octahydro-pyrano[3,2-b]pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 573 mg / Et₃N; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

2.1: 89 percent / DMSO; trifluoroacetic anhydride / CH₂Cl₂ / 1.5 h / -78 °C

3.1: potassium bis(trimethylsilyl)amide / toluene / 0.5 h / 80 - 90 °C

3.2: 84 percent / toluene / 0.5 h / 80 - 90 °C

With dmap; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; toluene;
DOI:10.1021/jo001433n

Reference yield:

: 328535-19-9
(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

: 328535-20-2
((2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-6-methoxy-3-methylene-octahydro-pyrano[3,2-b]pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 89 percent / DMSO; trifluoroacetic anhydride / CH₂Cl₂ / 1.5 h / -78 °C

2.1: potassium bis(trimethylsilyl)amide / toluene / 0.5 h / 80 - 90 °C

2.2: 84 percent / toluene / 0.5 h / 80 - 90 °C

With potassium hexamethylsilazane; dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; toluene;
DOI:10.1021/jo001433n