(3aR,5R,6R,6aR)-6-Allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6R,6aR)-6-Allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole
CAS No.:921202-70-2
Molecular Formula:C₂₁H₂₈O₅
Molecular Weight:360.45
Hs Code.:

Synonyms:(3aR,5R,6R,6aR)-6-Allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5R,6R,6aR)-6-Allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R,6R,6aR)-6-Allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 8 articles about (3aR,5R,6R,6aR)-6-Allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole 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:

: Methanesulfonic acid (R)-1-[(3aR,5R,6R,6aR)-6-allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-methanesulfonyloxy-ethyl ester

: 921202-70-2
(3aR,5R,6R,6aR)-6-Allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: With sodium iodide; In N,N-dimethyl-formamide; at 100 ℃; for 6h;
DOI:10.1021/jo061904r

Reference yield:

: 921202-53-1
1,2:5,6-di-O-isopropylidene-3-C-(1'-hydroxyethyl)-α-D-allo-1,4-furanose

: 921202-70-2
(3aR,5R,6R,6aR)-6-Allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran; various solvent(s) / 1 h / 0 °C

1.2: 88 percent / tetrahydrofuran; various solvent(s) / 72 h / 20 °C

2.1: NaH / tetrahydrofuran / 2 h / Heating

2.2: 97 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 95 °C

3.1: 88 percent / AcOH / H₂O / 48 h / 20 °C

4.1: triethylamine / CH₂Cl₂ / 1 h / 0 °C

5.1: 5.97 g / NaI / dimethylformamide / 6 h / 100 °C

With sodium hydride; acetic acid; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 5.1: Finklestein-type elimination;
DOI:10.1021/jo061904r

Reference yield:

: 921202-57-5
3-C-(2-benzyloxyethyl)-1,2:5,6-di-O-isopropylidene-D-allofuranose

: 921202-70-2
(3aR,5R,6R,6aR)-6-Allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 2 h / Heating

1.2: 97 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 95 °C

2.1: 88 percent / AcOH / H₂O / 48 h / 20 °C

3.1: triethylamine / CH₂Cl₂ / 1 h / 0 °C

4.1: 5.97 g / NaI / dimethylformamide / 6 h / 100 °C

With sodium hydride; acetic acid; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Finklestein-type elimination;
DOI:10.1021/jo061904r