(3aS,5S,6S,6aS)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxole

Base Information

Chemical Name:(3aS,5S,6S,6aS)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxole
CAS No.:320592-10-7
Molecular Formula:C₂₂H₂₆O₅
Molecular Weight:370.445
Hs Code.:

Synonyms:(3aS,5S,6S,6aS)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxole

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Chemical Property of (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxole

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Technology Process of (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxole

There total 10 articles about (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyltetrahydrofuro[3,2-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: 92.0%

: 100-39-0
benzyl bromide

: 172949-42-7
(3aS,5S,6S,6aS)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-ol

: 320592-10-7
(3aS,5S,6S,6aS)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxole

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 - 25 ℃;
DOI:10.1021/jo000510b

Reference yield: 72.0%

: 100-44-7
benzyl chloride

: 172949-42-7
(3aS,5S,6S,6aS)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-ol

: 320592-10-7
(3aS,5S,6S,6aS)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxole

Guidance literature:: (3aS,5S,6S,6aS)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-ol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.0833333h; Inert atmosphere; Reflux;

benzyl chloride; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 25 ℃; for 0.5h; Reflux;
DOI:10.1039/c3ob40374b

Reference yield:

: 41546-31-0
L-xylose

: 320592-10-7
(3aS,5S,6S,6aS)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 5 steps

1.1: CuSO₄; conc, H₂SO₄ / 4 h / 25 °C

1.2: 98 percent / aq. HCl / 1 h / 25 °C

2.1: 80 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: 87 percent / PDC; Ac₂O / CH₂Cl₂ / 2 h / Heating

4.1: 28 percent / NaBH₄ / ethanol; ethyl acetate / 1 h / 0 °C

5.1: 92 percent / NaH / tetrahydrofuran / 0 - 25 °C

With pyridine; sodium tetrahydroborate; dipyridinium dichromate; sulfuric acid; acetic anhydride; sodium hydride; copper(II) sulfate; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;
DOI:10.1021/jo000510b