1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol

Base Information

Chemical Name:1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol
CAS No.:321868-54-6
Molecular Formula:C₁₄H₁₈O₄
Molecular Weight:250.295
Hs Code.:

Synonyms:1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol

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Chemical Property of 1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol

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Technology Process of 1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol

There total 1 articles about 1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol 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:

: 4005-46-3
(1R)-1-[(3aR,5R,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol

: 321868-54-6
1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol

Guidance literature:: Multi-step reaction with 2 steps

1: aq. NaHCO₃; NaIO₄ / CH₂Cl₂; methanol / 2 h / 20 °C

2: tetrahydrofuran / 4.33 h / 0 °C

With sodium periodate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; 1: oxidative cleavage / 2: Addition;
DOI:10.1016/S0957-4166(00)00389-X

Reference yield: 95.0%

: 75-15-0,12122-00-8
carbon disulfide

: 321868-54-6
1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol

: 74-88-4
methyl iodide

: 321868-59-1
1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethyl-(1RS)-O-(S-methyl dithiocarbonate)

Guidance literature:: 1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol; With sodium hydride; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h;

carbon disulfide; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h;

methyl iodide; In tetrahydrofuran; hexane; at 0 - 20 ℃;
DOI:10.1016/S0957-4166(00)00389-X

Reference yield:

: 321868-54-6
1-[2,2-dimethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethan-(1RS)-ol

: 321868-49-9
3-hydroxy-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran; hexane / 0.25 h / 0 °C

1.2: tetrahydrofuran; hexane / 0.25 h / 0 °C

1.3: 95 percent / tetrahydrofuran; hexane / 0 - 20 °C

2.1: 79 percent / nBu₃SnH; AIBN / toluene / 6 h / Heating

3.1: 82 percent / aq. AcOH; H₂SO₄ / 6 h / 45 °C

4.1: 66 percent / Ag₂CO₃-Celite / benzene; dimethylformamide / 3 h / Heating

5.1: 80 percent / Ph₃P; DEAD / tetrahydrofuran / 8 h / 20 °C

6.1: 73 percent / MeONa; MeOH / CH₂Cl₂ / 0.25 h / -20 °C

With methanol; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; acetic acid; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1.1: Metallation / 1.2: Addition / 1.3: Methylation / 2.1: deoxygenation / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Mitsunobu reaction / 6.1: deacylation;
DOI:10.1016/S0957-4166(00)00389-X