6-benzyloxy-2,2-dimethyl-5-(1-methylene-allyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

Chemical Name:6-benzyloxy-2,2-dimethyl-5-(1-methylene-allyl)-tetrahydro-furo[2,3-d][1,3]dioxole
CAS No.:934493-25-1
Molecular Formula:C₁₈H₂₂O₄
Molecular Weight:302.37
Hs Code.:

6-benzyloxy-2,2-dimethyl-5-(1-methylene-allyl)-tetrahydro-furo[2,3-<i>d</i>][1,3]dioxole

Synonyms:6-benzyloxy-2,2-dimethyl-5-(1-methylene-allyl)-tetrahydro-furo[2,3-d][1,3]dioxole

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Chemical Property of 6-benzyloxy-2,2-dimethyl-5-(1-methylene-allyl)-tetrahydro-furo[2,3-d][1,3]dioxole

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Technology Process of 6-benzyloxy-2,2-dimethyl-5-(1-methylene-allyl)-tetrahydro-furo[2,3-d][1,3]dioxole

There total 7 articles about 6-benzyloxy-2,2-dimethyl-5-(1-methylene-allyl)-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: 89.0%

: 117174-46-6,53931-27-4
(3aR,5R,6S,6aR)-6-(benzyloxy)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

: 74-85-1
ethene

: 934493-25-1
6-benzyloxy-2,2-dimethyl-5-(1-methylene-allyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 80 ℃; for 12h;
DOI:10.1021/ol0701159

Reference yield:

: 53931-26-3
O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4

: 934493-25-1
6-benzyloxy-2,2-dimethyl-5-(1-methylene-allyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 2 steps

1: 74 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

2: 89 percent / Grubbs' second generation catalyst / toluene / 12 h / 80 °C

With n-butyllithium; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/ol0701159

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 934493-25-1
6-benzyloxy-2,2-dimethyl-5-(1-methylene-allyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / silica-supported NaIO₄ / CH₂Cl₂ / 2 h / 20 °C

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

2.2: 96 percent / CH₂Cl₂ / 13 h / 0 - 20 °C

3.1: 74 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

4.1: 89 percent / Grubbs' second generation catalyst / toluene / 12 h / 80 °C

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