(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

Base Information

Chemical Name:(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
CAS No.:631918-09-7
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 1 articles about (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 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: 24.0%

: 457645-20-4
1-phenyl-1,2-dideoxy-7-O-(phenoxythiocrbonyl)-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne

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

: 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

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

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 85 ℃; for 12h;
DOI:10.1016/S0957-4166(03)00532-9

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:

: 631918-09-7
(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

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

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 0 - 20 °C

1.2: 80 percent / dimethylformamide / 6 h / 20 °C

2.1: O₃ / methanol; CH₂Cl₂ / -78 °C

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

3.1: 142 mg / CeCl₃*H₂O; NaBH₄ / methanol / 0 - 20 °C

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

4.2: tetrahydrofuran / 1 h / 20 °C

4.3: 66 mg / tetrahydrofuran / 0.5 h / 20 °C

5.1: 90 percent / HBu₃Sn; AIBN / toluene / 0.5 h / 85 °C

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

7.1: 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; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0957-4166(03)00532-9