(2R,3R,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-4-methylene-octahydro-[2,2']bifuranyl

Base Information

Chemical Name:(2R,3R,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-4-methylene-octahydro-[2,2']bifuranyl
CAS No.:794517-35-4
Molecular Formula:C₂₅H₃₀O₅
Molecular Weight:410.51
Hs Code.:

Synonyms:(2R,3R,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-4-methylene-octahydro-[2,2']bifuranyl

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Chemical Property of (2R,3R,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-4-methylene-octahydro-[2,2']bifuranyl

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Technology Process of (2R,3R,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-4-methylene-octahydro-[2,2']bifuranyl

There total 5 articles about (2R,3R,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-4-methylene-octahydro-[2,2']bifuranyl 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: 78.0%

: 19493-09-5
Methylenetriphenylphosphorane

: 794517-34-3
(2R,3S,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-tetrahydro-[2,2']bifuranyl-4-one

: 794517-35-4
(2R,3R,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-4-methylene-octahydro-[2,2']bifuranyl

Guidance literature:: In tetrahydrofuran; diethyl ether; at 20 ℃; for 4h;
DOI:10.1016/j.tetlet.2004.08.143

Reference yield:

: 100-39-0
benzyl bromide

: 794517-35-4
(2R,3R,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-4-methylene-octahydro-[2,2']bifuranyl

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / NaH / dimethylformamide / 3 h / 20 °C

2: 86 percent / Amberlyst IR 120 / 9 h / Heating

3: 92 percent / IBX / dimethylsulfoxide / 3 h / 20 °C

4: 78 percent / tetrahydrofuran; diethyl ether / 4 h / 20 °C

With Amberlyst IR 120; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; 4: Wittig reaction;
DOI:10.1016/j.tetlet.2004.08.143

Reference yield:

: 209849-12-7
(1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol

: 794517-35-4
(2R,3R,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-4-methylene-octahydro-[2,2']bifuranyl

Guidance literature:: Multi-step reaction with 5 steps

1.1: HgCl₂ / H₂O / 1 h / 20 °C

1.2: O₂; NaBH₄ / dimethylformamide / 4 h / 20 °C

2.1: 94 percent / NaH / dimethylformamide / 3 h / 20 °C

3.1: 86 percent / Amberlyst IR 120 / 9 h / Heating

4.1: 92 percent / IBX / dimethylsulfoxide / 3 h / 20 °C

5.1: 78 percent / tetrahydrofuran; diethyl ether / 4 h / 20 °C

With Amberlyst IR 120; sodium hydride; mercury dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 5.1: Wittig reaction;
DOI:10.1016/j.tetlet.2004.08.143