(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole
CAS No.:912351-99-6
Molecular Formula:C₂₁H₃₀O₅
Molecular Weight:362.466
Hs Code.:

Synonyms:(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[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-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property:

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Technology Process of (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

There total 8 articles about (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[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: 78.0%

: 912351-95-2
6-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hexanal

: 1774-47-6
trimethylsulfoxonium iodide

: 912351-99-6
(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: With potassium tert-butylate; In dimethyl sulfoxide; at 0 ℃; for 1h;
DOI:10.1016/j.tetlet.2006.07.043

Reference yield:

: 912351-96-3
[(E)-6-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hex-5-enyloxy]-tert-butyl-diphenyl-silane

: 912351-99-6
(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / H₂ / PtO₂ / ethyl acetate / 12 h / 20 °C

2: 90 percent / TBAF / CH₂Cl₂ / 12 h / 20 °C

3: 95 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / 2 h / -78 °C

4: 78 percent / t-BuOK / dimethylsulfoxide / 1 h / 0 °C

With oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; platinum(IV) oxide; In dichloromethane; dimethyl sulfoxide; ethyl acetate; 3: Swern oxidation;
DOI:10.1016/j.tetlet.2006.07.043

Reference yield:

: 111-29-5
1 ,5-pentanediol

: 912351-99-6
(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 8 steps

1: 76 percent / imidazole / CH₂Cl₂ / 12 h / 0 °C

2: 82 percent / imidazole; I₂; PPh₃ / toluene / 0.5 h / 20 °C

3: 80 percent / toluene / 24 h / Heating

4: 74 percent / n-BuLi / tetrahydrofuran / 2 h / -78 °C

5: 93 percent / H₂ / PtO₂ / ethyl acetate / 12 h / 20 °C

6: 90 percent / TBAF / CH₂Cl₂ / 12 h / 20 °C

7: 95 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / 2 h / -78 °C

8: 78 percent / t-BuOK / dimethylsulfoxide / 1 h / 0 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; dimethyl sulfoxide; triethylamine; triphenylphosphine; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; 4: Wittig olefination / 7: Swern oxidation;
DOI:10.1016/j.tetlet.2006.07.043