(3aR,4S,6S,6aR)-2,2-dimethyl-6-((Z)-prop-1-en-1-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate

Base Information

Chemical Name:(3aR,4S,6S,6aR)-2,2-dimethyl-6-((Z)-prop-1-en-1-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate
CAS No.:1551543-56-6
Molecular Formula:C₁₇H₂₀O₅
Molecular Weight:304.343
Hs Code.:

Synonyms:(3aR,4S,6S,6aR)-2,2-dimethyl-6-((Z)-prop-1-en-1-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate

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Chemical Property of (3aR,4S,6S,6aR)-2,2-dimethyl-6-((Z)-prop-1-en-1-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate

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Technology Process of (3aR,4S,6S,6aR)-2,2-dimethyl-6-((Z)-prop-1-en-1-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate

There total 3 articles about (3aR,4S,6S,6aR)-2,2-dimethyl-6-((Z)-prop-1-en-1-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate 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:

: 1551543-54-4
(3aR,4S,6R,6aR)-6-formyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate

: 4736-60-1
ethyltriphenylphosphonium iodide

: 1551543-56-6
(3aR,4S,6S,6aR)-2,2-dimethyl-6-((Z)-prop-1-en-1-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate

Guidance literature:: ethyltriphenylphosphonium iodide; With potassium hexamethylsilazane; In tetrahydrofuran; at 20 ℃; for 2.25h;

In tetrahydrofuran; at -78 ℃; for 2h;

(3aR,4S,6R,6aR)-6-formyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate; In tetrahydrofuran; at -78 - 20 ℃; for 19h;
DOI:10.1021/ol500004k

Reference yield:

: 1551544-06-9
(3aR,4S,6S,6aR)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate

: 1551543-56-6
(3aR,4S,6S,6aR)-2,2-dimethyl-6-((Z)-prop-1-en-1-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: acetic acid / water / 20 h / 30 °C

2.1: sodium periodate; silica gel / dichloromethane / 0.5 h / 20 °C

3.1: potassium hexamethylsilazane / tetrahydrofuran / 2.25 h / 20 °C

3.2: 2 h / -78 °C

3.3: 19 h / -78 - 20 °C

With sodium periodate; silica gel; potassium hexamethylsilazane; acetic acid; In tetrahydrofuran; dichloromethane; water; 3.1: |Wittig Olefination;
DOI:10.1021/ol500004k

Reference yield:

: 1551543-45-3
(3aR,4S,6S,6aR)-6-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate

: 1551543-56-6
(3aR,4S,6S,6aR)-2,2-dimethyl-6-((Z)-prop-1-en-1-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium periodate; silica gel / dichloromethane / 0.5 h / 20 °C

2.1: potassium hexamethylsilazane / tetrahydrofuran / 2.25 h / 20 °C

2.2: 2 h / -78 °C

2.3: 19 h / -78 - 20 °C

With sodium periodate; silica gel; potassium hexamethylsilazane; In tetrahydrofuran; dichloromethane; 2.1: |Wittig Olefination;
DOI:10.1021/ol500004k