(3aS,5R,5aR,9aS,9bS)-8-{[(allyloxy)carbonyl]oxy}-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-5-yl 4-nitrobenzoate

Base Information

Chemical Name:(3aS,5R,5aR,9aS,9bS)-8-{[(allyloxy)carbonyl]oxy}-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-5-yl 4-nitrobenzoate
CAS No.:1429033-55-5
Molecular Formula:C₂₆H₃₁NO₉
Molecular Weight:501.533
Hs Code.:

Synonyms:(3aS,5R,5aR,9aS,9bS)-8-{[(allyloxy)carbonyl]oxy}-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-5-yl 4-nitrobenzoate

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Chemical Property of (3aS,5R,5aR,9aS,9bS)-8-{[(allyloxy)carbonyl]oxy}-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-5-yl 4-nitrobenzoate

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Technology Process of (3aS,5R,5aR,9aS,9bS)-8-{[(allyloxy)carbonyl]oxy}-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-5-yl 4-nitrobenzoate

There total 7 articles about (3aS,5R,5aR,9aS,9bS)-8-{[(allyloxy)carbonyl]oxy}-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-5-yl 4-nitrobenzoate 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: 59.0%

: 1429033-85-1
(R)-1-{(4S,5S)-5-[(E)-3-{[(allyloxy)carbonyl]oxy}-2-methylbuta-1,3-dien-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-3-methylbut-3-en-2-yl 4-nitrobenzoate

: 1429033-55-5
(3aS,5R,5aR,9aS,9bS)-8-{[(allyloxy)carbonyl]oxy}-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-5-yl 4-nitrobenzoate

Guidance literature:: With 2,6-di-tert-butyl-4-methyl-phenol; In 1,2-dichloro-benzene; at 180 ℃; for 24h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/jo400029u

Reference yield:

: 1429033-84-0
(R)-1-{(4S,5S)-2,2-dimethyl-5-[(E)-2-methyl-3-oxobut-1-en-1-yl]-1,3-dioxolan-4-yl}-3-methylbut-3-en-2-yl 4-nitrobenzoate

: 1429033-55-5
(3aS,5R,5aR,9aS,9bS)-8-{[(allyloxy)carbonyl]oxy}-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-5-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / 0.25 h / -78 °C / Inert atmosphere

1.2: 1 h / -50 °C / Inert atmosphere

2.1: 2,6-di-tert-butyl-4-methyl-phenol / 1,2-dichloro-benzene / 24 h / 180 °C / Inert atmosphere

With 2,6-di-tert-butyl-4-methyl-phenol; potassium hexamethylsilazane; In 1,2-dimethoxyethane; 1,2-dichloro-benzene; 2.1: |Diels-Alder Cycloaddition;
DOI:10.1021/jo400029u

Reference yield:

: 1429033-83-9
(R)-1-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-yl 4-nitrobenzoate

: 1429033-55-5
(3aS,5R,5aR,9aS,9bS)-8-{[(allyloxy)carbonyl]oxy}-2,2,5a,9-tetramethyl-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-d][1,3]dioxol-5-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere

2.2: 14 h / 20 °C / Inert atmosphere

3.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / 0.25 h / -78 °C / Inert atmosphere

3.2: 1 h / -50 °C / Inert atmosphere

4.1: 2,6-di-tert-butyl-4-methyl-phenol / 1,2-dichloro-benzene / 24 h / 180 °C / Inert atmosphere

With 2,6-di-tert-butyl-4-methyl-phenol; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-benzene; mineral oil; 4.1: |Diels-Alder Cycloaddition;
DOI:10.1021/jo400029u