(3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole
CAS No.:1351933-26-0
Molecular Formula:C₁₈H₂₀O₅
Molecular Weight:316.354
Hs Code.:

Synonyms:(3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

There total 6 articles about (3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[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: 67.0%

: C₂₅H₂₈O₈S

: 1351933-26-0
(3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: With sodium methylate; In methanol; at 0 - 20 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ol2029838

Reference yield:

: 1351933-22-6
(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

: 1351933-26-0
(3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 14 h / 0 - 20 °C / Inert atmosphere

2: sodium methylate / methanol / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; sodium methylate; In methanol;
DOI:10.1021/ol2029838

Reference yield:

: 35810-59-4
(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

: 1351933-26-0
(3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 50 °C / Inert atmosphere

1.2: 0.5 h / 0 °C / Inert atmosphere

2.1: acetic acid / water / 12 h / 20 °C / Inert atmosphere

3.1: pyridine / 14 h / 0 - 20 °C / Inert atmosphere

4.1: sodium methylate / methanol / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; sodium methylate; sodium hydride; acetic acid; In methanol; water; N,N-dimethyl-formamide;
DOI:10.1021/ol2029838