(1R,2R,3R)-2-Benzyloxy-1-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-pent-4-en-1-ol

Base Information

Chemical Name:(1R,2R,3R)-2-Benzyloxy-1-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-pent-4-en-1-ol
CAS No.:794517-40-1
Molecular Formula:C₂₅H₃₂O₄
Molecular Weight:396.527
Hs Code.:

Synonyms:(1R,2R,3R)-2-Benzyloxy-1-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-pent-4-en-1-ol

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Chemical Property of (1R,2R,3R)-2-Benzyloxy-1-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-pent-4-en-1-ol

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Technology Process of (1R,2R,3R)-2-Benzyloxy-1-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-pent-4-en-1-ol

There total 9 articles about (1R,2R,3R)-2-Benzyloxy-1-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-pent-4-en-1-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: 86.0%

: 19493-09-5
Methylenetriphenylphosphorane

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

: 794517-40-1
(1R,2R,3R)-2-Benzyloxy-1-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-pent-4-en-1-ol

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

: 794517-40-1
(1R,2R,3R)-2-Benzyloxy-1-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-pent-4-en-1-ol

Guidance literature:: Multi-step reaction with 7 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

5: 92 percent / H₂ / Pd-C / methanol / 0.33 h / 20 °C

6: 76 percent / AcOH / 4 h / 80 °C

7: 86 percent / tetrahydrofuran; diethyl ether / 4 h / 20 °C

With Amberlyst IR 120; hydrogen; sodium hydride; acetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; 4: Wittig reaction / 7: 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

: 794517-40-1
(1R,2R,3R)-2-Benzyloxy-1-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-pent-4-en-1-ol

Guidance literature:: Multi-step reaction with 8 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

6.1: 92 percent / H₂ / Pd-C / methanol / 0.33 h / 20 °C

7.1: 76 percent / AcOH / 4 h / 80 °C

8.1: 86 percent / tetrahydrofuran; diethyl ether / 4 h / 20 °C

With Amberlyst IR 120; hydrogen; sodium hydride; acetic acid; mercury dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 5.1: Wittig reaction / 8.1: Wittig reaction;
DOI:10.1016/j.tetlet.2004.08.143