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

Base Information

Chemical Name:1-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone
CAS No.:263544-57-6
Molecular Formula:C₁₆H₂₀O₅
Molecular Weight:292.332
Hs Code.:

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

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

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

There total 1 articles about 1-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone 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: 72.0%

: (3aR,5R,6S,6aR)-6-Benzyloxy-5-(2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

: 263544-57-6
1-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone

Guidance literature:: (3aR,5R,6S,6aR)-6-Benzyloxy-5-(2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole; With sodium t-butanolate; In tetrahydrofuran;

With sulfuric acid;
DOI:10.1016/S0040-4039(99)02158-9

Reference yield:

: 263544-57-6
1-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone

: 98611-68-8
2,2-Dimethyl-propionic acid (1R,6R,7R,8S,9R)-7-benzyloxy-9-methyl-4,12-dioxo-10-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-8-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) Et₂O, -78 deg C

2: 81 percent / 6N H₂SO₄ / tetrahydrofuran / 12 h / 40 °C

3: NaIO₄, NaHCO₃ / tetrahydrofuran / 0 °C

4: toluene / 12 h / 40 °C

5: 4-DMAP

6: Et₃N / diethyl ether

7: L-selectride / diethyl ether / -78 °C

8: NaH, EtOH

9: K₂CO₃ / acetone

10: Al(CH₃)3 / CH₂Cl₂ / -20 °C

11: 70 percent / H₂SO₄ / dioxane; H₂O

With dmap; sodium periodate; ethanol; sulfuric acid; trimethylaluminum; L-Selectride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; acetone; toluene;
DOI:10.1021/jo00220a064

Reference yield:

: 263544-57-6
1-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone

: 98611-71-3
2,2-Dimethyl-propionic acid (E)-(1S,2R)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((R)-2-methyl-3-oxo-2,3-dihydro-furan-2-yl)-hexa-3,5-dienyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) Et₂O, -78 deg C

2: 81 percent / 6N H₂SO₄ / tetrahydrofuran / 12 h / 40 °C

3: NaIO₄, NaHCO₃ / tetrahydrofuran / 0 °C

4: toluene / 12 h / 40 °C

5: 4-DMAP

6: Et₃N / diethyl ether

With dmap; sodium periodate; sulfuric acid; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1021/jo00220a064