(4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Base Information

Chemical Name:(4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
CAS No.:89872-84-4
Molecular Formula:C₁₆H₂₀O₆
Molecular Weight:308.331
Hs Code.:

Synonyms:(4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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Chemical Property of (4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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Technology Process of (4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

There total 6 articles about (4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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: 90.0%

: 89889-10-1
Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside

: 89872-84-4
(2R,4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Ambient temperature;
DOI:10.1021/jo00187a010

Reference yield:

: 112711-35-0
methyl 3-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-[(R)-phenylmethylene]-α-D-glucopyranoside

: 89872-84-4
(2R,4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / dimethylsulfoxide, trifluoracetic anhydride / CH₂Cl₂ / 0.5 h / -78 °C

2: 90 percent / acetonitrile / Heating

3: 90 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

With lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo00187a010

Reference yield:

: 78342-32-2
Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-2-uloside

: 89872-84-4
(2R,4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / acetonitrile / Heating

2: 90 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

3: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

With lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; acetonitrile;
DOI:10.1021/jo00187a010