(1S,2R,3S)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde

Base Information

Chemical Name:(1S,2R,3S)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde
CAS No.:1428245-82-2
Molecular Formula:C₁₇H₂₃NO₅
Molecular Weight:321.373
Hs Code.:

Synonyms:(1S,2R,3S)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde

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Chemical Property of (1S,2R,3S)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde

Chemical Property:

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Technology Process of (1S,2R,3S)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde

There total 8 articles about (1S,2R,3S)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde 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:

: (E)-6-((4-methoxybenzyl)oxy)-2-methyl-8-nitrooct-7-enal

: 1428245-60-6
(1S,2R,3R)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde

: 1428245-74-2
(1R,2R,3R)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde

: 1428245-82-2
(1S,2R,3S)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde

: 1428245-86-6
(1R,2R,3S)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde

Guidance literature:: With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; In methanol; at 25 ℃; Overall yield = 88 %; diastereoselective reaction;
DOI:10.1016/j.tet.2013.02.078

Reference yield:

: 6-((tert-butyldimethylsilyl)oxy)-2-methylhexanal

: 1428245-82-2
(1S,2R,3S)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 °C

2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 2 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

3.1: ammonium chloride / tetrahydrofuran / -78 - 30 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

4.2: 12 h / 20 °C

5.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; sodium periodate / diethyl ether; water / 24 h / 20 °C

6.1: triethylamine / 15 h / 20 °C

6.2: 2 h / -78 °C / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane; water / 18 h / 0 - 20 °C

8.1: L-proline / methanol / 25 °C

With sodium periodate; osmium(VIII) oxide; oxalyl dichloride; boron trifluoride diethyl etherate; sodium hydride; ammonium chloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; L-proline; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 2.2: |Swern Oxidation / 6.2: |Henry Nitro Aldol Condensation / 8.1: |Michael Addition;
DOI:10.1016/j.tet.2013.02.078

Reference yield:

: 1428245-64-0
5-(1,3-dioxan-2-yl)hexan-1-ol

: 1428245-82-2
(1S,2R,3S)-3-(4-methoxybenzyloxy)-1-methyl-2-(nitromethyl)cyclohexanecarbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 2 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: ammonium chloride / tetrahydrofuran / -78 - 30 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

3.2: 12 h / 20 °C

4.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; sodium periodate / diethyl ether; water / 24 h / 20 °C

5.1: triethylamine / 15 h / 20 °C

5.2: 2 h / -78 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane; water / 18 h / 0 - 20 °C

7.1: L-proline / methanol / 25 °C

With sodium periodate; osmium(VIII) oxide; oxalyl dichloride; sodium hydride; ammonium chloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; L-proline; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 1.2: |Swern Oxidation / 5.2: |Henry Nitro Aldol Condensation / 7.1: |Michael Addition;
DOI:10.1016/j.tet.2013.02.078