(3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-4-(benzyloxy)-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxine

Base Information

Chemical Name:(3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-4-(benzyloxy)-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxine
CAS No.:631918-14-4
Molecular Formula:C₂₇H₃₂O₅
Molecular Weight:436.548
Hs Code.:

Synonyms:(3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-4-(benzyloxy)-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxine

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Chemical Property of (3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-4-(benzyloxy)-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxine

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Technology Process of (3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-4-(benzyloxy)-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxine

There total 1 articles about (3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-4-(benzyloxy)-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxine 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: 80.0%

: 100-39-0
benzyl bromide

: 631918-09-7
(3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-ol

: 631918-14-4
(3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-4-(benzyloxy)-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxine

Guidance literature:: (3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-ol; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 6h;
DOI:10.1016/S0957-4166(03)00532-9

Reference yield:

: 631918-14-4
(3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-4-(benzyloxy)-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxine

: (3aS,4S,5aS,9aR,9bS)-4-Benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-one

Guidance literature:: (3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-4-(benzyloxy)-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxine; With ozone; In methanol; dichloromethane; at -78 ℃;

With dimethylsulfide; In methanol; dichloromethane; at -78 - 20 ℃; for 3h;
DOI:10.1016/S0957-4166(03)00532-9

Reference yield:

: 631918-14-4
(3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-4-(benzyloxy)-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxine

: 156619-13-5
(1R,2R,3S,4R,5S)-5-Hydroxymethyl-cyclohexane-1,2,3,4-tetraol

Guidance literature:: Multi-step reaction with 6 steps

1.1: O₃ / methanol; CH₂Cl₂ / -78 °C

1.2: Me₂S / methanol; CH₂Cl₂ / 3 h / -78 - 20 °C

2.1: 142 mg / CeCl₃*H₂O; NaBH₄ / methanol / 0 - 20 °C

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: tetrahydrofuran / 1 h / 20 °C

3.3: 66 mg / tetrahydrofuran / 0.5 h / 20 °C

4.1: 90 percent / HBu₃Sn; AIBN / toluene / 0.5 h / 85 °C

5.1: H₂ / Pd/C / methanol / 1 h / 20 °C / 1810.02 Torr

6.1: AcOH / tetrahydrofuran; H₂O / 85 °C

With sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium hydride; ozone; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1016/S0957-4166(03)00532-9