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

Base Information

Chemical Name:(3aR,4S,5aS,9aR,9bS)-4-Benzyloxy-2,2,8,8-tetramethyl-5-methylene-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxine
CAS No.:474103-98-5
Molecular Formula:C₂₁H₂₈O₅
Molecular Weight:360.45
Hs Code.:

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

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Chemical Property of (3aR,4S,5aS,9aR,9bS)-4-Benzyloxy-2,2,8,8-tetramethyl-5-methylene-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxine

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Technology Process of (3aR,4S,5aS,9aR,9bS)-4-Benzyloxy-2,2,8,8-tetramethyl-5-methylene-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxine

There total 5 articles about (3aR,4S,5aS,9aR,9bS)-4-Benzyloxy-2,2,8,8-tetramethyl-5-methylene-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxine 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

: 474103-76-9
(3aR,4S,5aS,9aR,9bS)-2,2,8,8-Tetramethyl-5-methylene-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ol

: 474103-98-5
(3aR,4S,5aS,9aR,9bS)-4-Benzyloxy-2,2,8,8-tetramethyl-5-methylene-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxine

Guidance literature:: With sodium hydride;
DOI:10.1016/S0040-4039(02)01121-8

Reference yield:

: 474103-74-7
Carbonic acid ethyl ester (3aR,4S,5aS,9aR,9bS)-2,2,8,8-tetramethyl-5-methylene-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl ester

: 474103-98-5
(3aR,4S,5aS,9aR,9bS)-4-Benzyloxy-2,2,8,8-tetramethyl-5-methylene-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / K₂CO₃ / methanol

2: 80 percent / NaH; Bu₄NI / tetrahydrofuran / 3 h

With tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol;
DOI:10.1002/ejoc.200300339

Reference yield:

: 357604-61-6
2,3:4,6-di-O-isopropylidene-D-mannopyranose

: 474103-98-5
(3aR,4S,5aS,9aR,9bS)-4-Benzyloxy-2,2,8,8-tetramethyl-5-methylene-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 6 steps

1: 68 percent / BuLi / hexane; tetrahydrofuran / 10 h / -78 - 20 °C

2: 57 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

3: 76 percent / pyridine / acetonitrile / 1 h / 85 °C

4: 23 percent / Bu₃SnH; AIBN / toluene / 12 h / 85 °C

5: 70 percent / K₂CO₃ / methanol

6: 80 percent / NaH; Bu₄NI / tetrahydrofuran / 3 h

With pyridine; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1002/ejoc.200300339