(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((Z)-but-1-en-1-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((Z)-but-1-en-1-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
CAS No.:98760-37-3
Molecular Formula:C₁₈H₂₄O₄
Molecular Weight:304.386
Hs Code.:

Synonyms:(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((Z)-but-1-en-1-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((Z)-but-1-en-1-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((Z)-but-1-en-1-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

There total 8 articles about (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((Z)-but-1-en-1-yl)-2,2-dimethyltetrahydrofuro[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: 85.0%

: 6228-47-3
n-propyltriphenylphosphonium bromide

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 98760-37-3
(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((Z)-but-1-en-1-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 20h; stereoselective reaction;
DOI:10.1021/ol400528g

Reference yield:

: 100-39-0
benzyl bromide

: 98760-37-3
(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((Z)-but-1-en-1-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 10 h / 70 °C

2: acetic acid / water / 5 h / 55 °C

3: sodium periodate / water; methanol / 0.75 h

4: n-butyllithium / tetrahydrofuran / 20 h / -78 - 20 °C

With sodium periodate; n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; methanol; water; 4: |Wittig Olefination;
DOI:10.1021/ol400528g

Reference yield:

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 98760-37-3
(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((Z)-but-1-en-1-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 10 h / 70 °C

2: acetic acid / water / 5 h / 55 °C

3: sodium periodate / water; methanol / 0.75 h

4: n-butyllithium / tetrahydrofuran / 20 h / -78 - 20 °C

With sodium periodate; n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; methanol; water; 4: |Wittig Olefination;
DOI:10.1021/ol400528g