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

Base Information

Chemical Name:(2R,3S,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-tetrahydro-[2,2']bifuranyl-4-one
CAS No.:794517-34-3
Molecular Formula:C₂₄H₂₈O₆
Molecular Weight:412.483
Hs Code.:

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

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

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

There total 5 articles about (2R,3S,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-tetrahydro-[2,2']bifuranyl-4-one 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: 92.0%

: 794517-33-2
(2R,3R,4R,5R,2'S,5'R)-3-Benzyloxy-5'-benzyloxymethyl-5-methoxy-octahydro-[2,2']bifuranyl-4-ol

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

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 3h;
DOI:10.1016/j.tetlet.2004.08.143

Reference yield:

: 100-39-0
benzyl bromide

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

Guidance literature:: Multi-step reaction with 3 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

With Amberlyst IR 120; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; N,N-dimethyl-formamide;
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

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

Guidance literature:: Multi-step reaction with 4 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

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