(1S,4aR,5R,8aS)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene

Base Information

Chemical Name:(1S,4aR,5R,8aS)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene
CAS No.:1302981-66-3
Molecular Formula:C₂₁H₂₇NO₄
Molecular Weight:357.45
Hs Code.:

Synonyms:(1S,4aR,5R,8aS)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene

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Chemical Property of (1S,4aR,5R,8aS)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene

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Technology Process of (1S,4aR,5R,8aS)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene

There total 4 articles about (1S,4aR,5R,8aS)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene 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:

: 1302981-65-2
C₂₁H₂₇NO₄

: 1302981-67-4
(1S,4aS,5S,8aR)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene

: 1302981-66-3
(1S,4aR,5R,8aS)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene

Guidance literature:: With 2,6-di-tert-butyl-4-methyl-phenol; In toluene; at 90 ℃; for 16h; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetlet.2010.11.012

Reference yield:

: 1302981-89-0
C₂₁H₂₆O₄

: 1302981-67-4
(1S,4aS,5S,8aR)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene

: 1302981-66-3
(1S,4aR,5R,8aS)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran / -78 °C

1.2: -78 °C

2.1: diisobutylaluminium hydride / -78 °C

3.1: chloro-trimethyl-silane; tetrabutyl ammonium fluoride; triethylamine / tetrahydrofuran

4.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 16 h / 90 °C / Inert atmosphere

With chloro-trimethyl-silane; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; toluene; 3.1: Henry reaction / 4.1: Intramolecular Diels-Alder reaction;
DOI:10.1016/j.tetlet.2010.11.012

Reference yield:

: 1302981-90-3
C₂₂H₃₀O₄

: 1302981-67-4
(1S,4aS,5S,8aR)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene

: 1302981-66-3
(1S,4aR,5R,8aS)-1-(((4-methoxybenzyl)oxy)methyl)-1,3-dimethyl-5-nitro-1,2,4a,5,6,8a-hexahydronaphthalene

Guidance literature:: Multi-step reaction with 3 steps

1: diisobutylaluminium hydride / -78 °C

2: chloro-trimethyl-silane; tetrabutyl ammonium fluoride; triethylamine / tetrahydrofuran

3: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 16 h / 90 °C / Inert atmosphere

With chloro-trimethyl-silane; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; toluene; 2: Henry reaction / 3: Intramolecular Diels-Alder reaction;
DOI:10.1016/j.tetlet.2010.11.012