(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol

Base Information

Chemical Name:(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol
CAS No.:1351933-29-3
Molecular Formula:C₁₉H₂₂O₅
Molecular Weight:330.381
Hs Code.:

Synonyms:(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol

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Chemical Property of (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol

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Technology Process of (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol

There total 7 articles about (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-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: 97.0%

: 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

: 2181-42-2
trimethylsulphonium iodide

: 1351933-29-3
(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol

Guidance literature:: trimethylsulphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at -10 ℃; for 1h; Inert atmosphere;

(3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole; In tetrahydrofuran; hexane; at -10 - 20 ℃; for 1h; 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

: 1351933-29-3
(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

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

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

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -10 °C / Inert atmosphere

3.2: 1 h / -10 - 20 °C / Inert atmosphere

With pyridine; n-butyllithium; sodium methylate; In tetrahydrofuran; methanol; hexane;
DOI:10.1021/ol2029838

Reference yield:

: 100-39-0
benzyl bromide

: 1351933-29-3
(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 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

5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -10 °C / Inert atmosphere

5.2: 1 h / -10 - 20 °C / Inert atmosphere

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