(3aR,5R,6R,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6R,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole
CAS No.:115079-02-2
Molecular Formula:C₂₄H₃₀O₄
Molecular Weight:382.5
Hs Code.:

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

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

There total 6 articles about (3aR,5R,6R,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-5-phenethyl-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: 90.0%

: 100-44-7
benzyl chloride

: 115092-22-3
2-((3aR,5R,6R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-ethanol

: 115079-02-2
(3aR,5R,6R,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 22 ℃; for 4h;
DOI:10.1021/ja00222a024

Reference yield:

: 19029-63-1
3-C-(carbomethoxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

: 115079-02-2
(3aR,5R,6R,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) lead tetraacetate; 2.) K₂CO₃ / 1.) CH₂Cl₂, 22 deg C, 2 h; 2.) CH₂Cl₂, 1 h

2: tetrahydrofuran / 13 h / 22 °C

3: H₂ / Pd/C / methanol / 1500.1 Torr

4: 1.) p-toluenesulfonic acid; 2.) lithium aluminum hydride / 1.) methanol-water, 8 h; 2.) THF, reflux, 1 h

5: 90 percent / sodium hydride / dimethylformamide / 4 h / 22 °C

With lead(IV) acetate; lithium aluminium tetrahydride; hydrogen; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00222a024

Reference yield:

: 18427-18-4
1,2:5,6-di-O-isopropylidene-3-deoxy-3-(methoxycarbonyl-methyl)-α-D-allofuranoside

: 115079-02-2
(3aR,5R,6R,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 6 steps

1: AcOH/water / 37 h / 22 °C

2: 1.) lead tetraacetate; 2.) K₂CO₃ / 1.) CH₂Cl₂, 22 deg C, 2 h; 2.) CH₂Cl₂, 1 h

3: tetrahydrofuran / 13 h / 22 °C

4: H₂ / Pd/C / methanol / 1500.1 Torr

5: 1.) p-toluenesulfonic acid; 2.) lithium aluminum hydride / 1.) methanol-water, 8 h; 2.) THF, reflux, 1 h

6: 90 percent / sodium hydride / dimethylformamide / 4 h / 22 °C

With lead(IV) acetate; lithium aluminium tetrahydride; water; hydrogen; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00222a024