(3aS,4R,5aR,9aR,9bS)-5-benzylidene-2,2,8,8-tetra-methylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-yl tert-butyl(dimethyl)silyl ether

Base Information

Chemical Name:(3aS,4R,5aR,9aR,9bS)-5-benzylidene-2,2,8,8-tetra-methylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-yl tert-butyl(dimethyl)silyl ether
CAS No.:221044-99-1
Molecular Formula:C₂₆H₄₀O₅Si
Molecular Weight:460.686
Hs Code.:

Synonyms:(3aS,4R,5aR,9aR,9bS)-5-benzylidene-2,2,8,8-tetra-methylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-yl tert-butyl(dimethyl)silyl ether

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Chemical Property of (3aS,4R,5aR,9aR,9bS)-5-benzylidene-2,2,8,8-tetra-methylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-yl tert-butyl(dimethyl)silyl ether

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Technology Process of (3aS,4R,5aR,9aR,9bS)-5-benzylidene-2,2,8,8-tetra-methylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-yl tert-butyl(dimethyl)silyl ether

There total 8 articles about (3aS,4R,5aR,9aR,9bS)-5-benzylidene-2,2,8,8-tetra-methylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-yl tert-butyl(dimethyl)silyl ether 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: 58.0%

: 221044-98-0
1-phenyl-1,2-dideoxy-7-O-(phenoxythiocrbonyl)-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne

: 221044-99-1
(3aS,4R,5aR,9aR,9bS)-5-benzylidene-2,2,8,8-tetra-methylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-yl tert-butyl(dimethyl)silyl ether

: (3aS,4R,5aS,9aR,9bS)-5-benzylidene-2,2,8,8-tetra-methylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-yl tert-butyl(dimethyl)silyl ether

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 85 ℃; for 12h;
DOI:10.1016/S0957-4166(03)00532-9

Reference yield:

: 221044-98-0
1-phenyl-1,2-dideoxy-7-O-(phenoxythiocrbonyl)-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne

: 221044-99-1
(3aS,4R,5aR,9aR,9bS)-5-benzylidene-2,2,8,8-tetra-methylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-yl tert-butyl(dimethyl)silyl ether

: tert-Butyl-dimethyl-{(3aS,4R,5aS,9aR,9bS)-2,2,8,8-tetramethyl-5-[1-phenyl-meth-(E)-ylidene]-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yloxy}-silane

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃; Yield given; Yields of byproduct given;
DOI:10.1039/a808848i

Reference yield:

: 357604-61-6
2,3:4,6-di-O-isopropylidene-D-mannopyranose

: 221044-99-1
(3aS,4R,5aR,9aR,9bS)-5-benzylidene-2,2,8,8-tetra-methylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-yl tert-butyl(dimethyl)silyl ether

Guidance literature:: Multi-step reaction with 4 steps

1.1: BuLi / tetrahydrofuran; hexane / -78 °C

1.2: 57 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 65 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / 20 °C

3.1: 85 percent / pyridine / acetonitrile / 1 h / 85 °C

4.1: 38 percent / HBu₃Sn; AIBN / toluene / 12 h / 85 °C

With pyridine; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0957-4166(03)00532-9