4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

Base Information

Chemical Name:4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
CAS No.:26255-73-2
Molecular Formula:C₁₃H₂₂O₆
Molecular Weight:274.314
Hs Code.:

Synonyms:4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

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Chemical Property of 4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

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Technology Process of 4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

There total 1 articles about 4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-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:

: 67-56-1
methanol

: 38838-12-9
2,3:5,6-Di-O-isopropyliden-α-D-mannofuranosyl-bromid

: 617-04-9
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

: 26255-72-1
Methyl-2,3:5,6-di-O-isopropyliden-β-D-mannofuranosid

: 26255-73-2
4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

Guidance literature:: Yield given. Yields of byproduct given;

Reference yield:

: 26255-73-2
4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

: 4-(6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-phthalic acid dimethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 81 percent / aq. acetic acid / 8 h / 20 °C

2.1: 86 percent / silica-supported NaIO₄ / CH₂Cl₂ / 2 h / 20 °C

3.1: triphenylphosphine; zinc / CH₂Cl₂ / 0.25 h / 0 °C

3.2: 96 percent / CH₂Cl₂ / 13 h / 0 - 20 °C

4.1: 91 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

5.1: 89 percent / Grubbs' second generation catalyst / toluene / 12 h / 80 °C

6.1: DMAD / toluene / Heating

6.2: 81 percent / MnO₂ / CH₂Cl₂ / 12 h / Heating

With sodium periodate; n-butyllithium; silica gel; acetic acid; triphenylphosphine; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; toluene; 6.1: Diels-Alder reaction;
DOI:10.1021/ol0701159

Reference yield:

: 26255-73-2
4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

: 40823-53-8
methyl 2,3-O-isopropylidene-6-O-tosyl-α-D-lyxo-hexofuranos-5-ulose

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / 80percent AcOH / 0.75 h / 60 °C

2: 90 percent / pyridine / 12 h / 20 °C

3: 96 percent / pyridinium chlorochromate / CH₂Cl₂ / 6 h / 20 °C / molecular sieves 3A

With pyridine; acetic acid; pyridinium chlorochromate; In dichloromethane;
DOI:10.1246/bcsj.66.2315