(3aS,4S,5R,5aR,8aR,8bS)-hexahydro-5-hydroxy-2,2,7,7-tetramethylbenzo[1,2-d:3,4-d]bis[1,3]dioxol-4-yl (2E)-3-phenylprop-2-enoate

Base Information

Chemical Name:(3aS,4S,5R,5aR,8aR,8bS)-hexahydro-5-hydroxy-2,2,7,7-tetramethylbenzo[1,2-d:3,4-d]bis[1,3]dioxol-4-yl (2E)-3-phenylprop-2-enoate
CAS No.:1413941-01-1
Molecular Formula:C₂₁H₂₆O₇
Molecular Weight:390.433
Hs Code.:

Synonyms:(3aS,4S,5R,5aR,8aR,8bS)-hexahydro-5-hydroxy-2,2,7,7-tetramethylbenzo[1,2-d:3,4-d]bis[1,3]dioxol-4-yl (2E)-3-phenylprop-2-enoate

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Chemical Property of (3aS,4S,5R,5aR,8aR,8bS)-hexahydro-5-hydroxy-2,2,7,7-tetramethylbenzo[1,2-d:3,4-d]bis[1,3]dioxol-4-yl (2E)-3-phenylprop-2-enoate

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Technology Process of (3aS,4S,5R,5aR,8aR,8bS)-hexahydro-5-hydroxy-2,2,7,7-tetramethylbenzo[1,2-d:3,4-d]bis[1,3]dioxol-4-yl (2E)-3-phenylprop-2-enoate

There total 1 articles about (3aS,4S,5R,5aR,8aR,8bS)-hexahydro-5-hydroxy-2,2,7,7-tetramethylbenzo[1,2-d:3,4-d]bis[1,3]dioxol-4-yl (2E)-3-phenylprop-2-enoate 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: 87.0%

: 63073-96-1
potassium cinnamate

: 151593-08-7
(1S,2R,3R,4S,5S,6R)-3,4;5,6-bis(isopropylidenedioxy)-1,2-epoxycyclohexane

: 1413941-01-1
(3aS,4S,5R,5aR,8aR,8bS)-hexahydro-5-hydroxy-2,2,7,7-tetramethylbenzo[1,2-d:3,4-d]bis[1,3]dioxol-4-yl (2E)-3-phenylprop-2-enoate

Guidance literature:: With 18-crown-6 ether; (E)-3-phenylacrylic acid; tetra-(n-butyl)ammonium iodide; In N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; N,N-dimethyl-formamide; at 127 ℃; Inert atmosphere;
DOI:10.1002/hlca.201200432 DOI:10.1002/hlca.201200432

Reference yield: 78.0%

: 32775-95-4
(E)-3,5-hexadienoic acid

: 1413941-01-1
(3aS,4S,5R,5aR,8aR,8bS)-hexahydro-5-hydroxy-2,2,7,7-tetramethylbenzo[1,2-d:3,4-d]bis[1,3]dioxol-4-yl (2E)-3-phenylprop-2-enoate

: 1413941-02-2
(3aS,4R,5R,5aS,8aS,8bS)-hexahydro-2,2,7,7-tetramethyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}benzo[1,2-d:3,4-d’]bis[1,3]dioxol-4-yl (3E)-hexa-3,5-dienoate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;
DOI:10.1002/hlca.201200432 DOI:10.1002/hlca.201200432

Reference yield:

: 1413941-01-1
(3aS,4S,5R,5aR,8aR,8bS)-hexahydro-5-hydroxy-2,2,7,7-tetramethylbenzo[1,2-d:3,4-d]bis[1,3]dioxol-4-yl (2E)-3-phenylprop-2-enoate

: 1413941-03-3
(1S,2S,3S,4S,4aR,6aS,7S,10aR,13aR)-1,2;3,4-di(isopropylidenedioxy)-7-phenyl-2,3,4,4a,6a,7,10a,11-octahydro-1H-dibenzo[b,f][1,4]dioxonine-6,12(10H,13aH)-dione

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 3 h / 0 °C / Inert atmosphere

2: 141 °C / Inert atmosphere

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; 2: |Diels-Alder Cycloaddition;
DOI:10.1002/hlca.201200432 DOI:10.1002/hlca.201200432