(2R,3S,4R,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran

Base Information

Chemical Name:(2R,3S,4R,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran
CAS No.:850353-31-0
Molecular Formula:C₁₉H₂₈O₄
Molecular Weight:320.429
Hs Code.:

Synonyms:(2R,3S,4R,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran

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Chemical Property of (2R,3S,4R,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran

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Technology Process of (2R,3S,4R,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran

There total 4 articles about (2R,3S,4R,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran 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: 100.0%

: 850353-29-6
(2R,3S,4R,6R)-6-Benzyloxymethyl-3-methyl-2-((E)-propenyl)-tetrahydro-pyran-4-ol

: 107-30-2
chloromethyl methyl ether

: 850353-31-0
(2R,3S,4R,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2005.01.121

Reference yield:

: 115560-90-2
(2R)-(E)-1-(phenylmethoxy)-4-hexen-2-ol

: 850353-31-0
(2R,3S,4R,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1.1: TFA / CH₂Cl₂ / 3 h / 0 °C

1.2: K₂CO₃ / methanol / 1 h / 20 °C

2.1: 100 percent / (i-Pr)2NEt; DMAP / CH₂Cl₂ / 12 h / 0 - 20 °C

With dmap; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; 1.1: Prins cyclisation;
DOI:10.1016/j.tetlet.2005.01.121

Reference yield:

: 171075-74-4
(2R)-1-(benzyloxy)hex-4-yn-2-ol

: 850353-31-0
(2R,3S,4R,6R)-6-Benzyloxymethyl-4-methoxymethoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 86 percent / Na / liquid ammonia; tetrahydrofuran / 5 h

2.1: 65 percent / NaH / dimethylformamide / 6 h / 0 - 20 °C

3.1: TFA / CH₂Cl₂ / 3 h / 0 °C

3.2: K₂CO₃ / methanol / 1 h / 20 °C

4.1: 100 percent / (i-Pr)2NEt; DMAP / CH₂Cl₂ / 12 h / 0 - 20 °C

With dmap; sodium; sodium hydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; ammonia; N,N-dimethyl-formamide; 1.1: Birch reduction / 3.1: Prins cyclisation;
DOI:10.1016/j.tetlet.2005.01.121