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

Base Information

Chemical Name:6-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hexanal
CAS No.:912351-95-2
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

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

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Chemical Property of 6-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hexanal

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Technology Process of 6-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hexanal

There total 7 articles about 6-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hexanal 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: 95.0%

: 912351-98-5
6-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hexan-1-ol

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

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 2h;
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

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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 111-29-5
1 ,5-pentanediol

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

Guidance literature:: Multi-step reaction with 7 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

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