(3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]pyran

Base Information

Chemical Name:(3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]pyran
CAS No.:921202-75-7
Molecular Formula:C₁₉H₂₄O₅
Molecular Weight:332.397
Hs Code.:

Synonyms:(3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]pyran

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Chemical Property of (3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]pyran

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Technology Process of (3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]pyran

There total 9 articles about (3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]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: 93.0%

: 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

: 921202-75-7
(3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]pyran

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; at 20 ℃;
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

: 921202-75-7
(3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]pyran

Guidance literature:: Multi-step reaction with 6 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

6.1: 93 percent / Grubbs first-generation catalyst / CH₂Cl₂ / 20 °C

With sodium hydride; acetic acid; triethylamine; sodium iodide; Grubbs catalyst first generation; 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

: 921202-75-7
(3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]pyran

Guidance literature:: Multi-step reaction with 5 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

5.1: 93 percent / Grubbs first-generation catalyst / CH₂Cl₂ / 20 °C

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