(2S,4aR,8aR)-cis-2-[8-(4-methoxy-benzyloxymethyl)-4a-methyl-1,2,4a,8a-tetrahydronaphthalen-2-yl]-propionic acid

Base Information

Chemical Name:(2S,4aR,8aR)-cis-2-[8-(4-methoxy-benzyloxymethyl)-4a-methyl-1,2,4a,8a-tetrahydronaphthalen-2-yl]-propionic acid
CAS No.:545374-96-7
Molecular Formula:C₂₃H₂₈O₄
Molecular Weight:368.473
Hs Code.:

Synonyms:(2S,4aR,8aR)-cis-2-[8-(4-methoxy-benzyloxymethyl)-4a-methyl-1,2,4a,8a-tetrahydronaphthalen-2-yl]-propionic acid

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Chemical Property of (2S,4aR,8aR)-cis-2-[8-(4-methoxy-benzyloxymethyl)-4a-methyl-1,2,4a,8a-tetrahydronaphthalen-2-yl]-propionic acid

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Technology Process of (2S,4aR,8aR)-cis-2-[8-(4-methoxy-benzyloxymethyl)-4a-methyl-1,2,4a,8a-tetrahydronaphthalen-2-yl]-propionic acid

There total 7 articles about (2S,4aR,8aR)-cis-2-[8-(4-methoxy-benzyloxymethyl)-4a-methyl-1,2,4a,8a-tetrahydronaphthalen-2-yl]-propionic acid 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: 93.0%

: 545374-86-5
2-[(2S,4aS,8aR)-1,2,4a,8a-tetrahydro-8-[[(4-methoxybenzyl)oxy]methyl]-4a-methylnaphthalen-2-yl]-2-methylpropanedioic acid dimethyl ester

: 545374-96-7
(2S,4aR,8aR)-cis-2-[8-(4-methoxy-benzyloxymethyl)-4a-methyl-1,2,4a,8a-tetrahydronaphthalen-2-yl]-propionic acid

Guidance literature:: With sodium hydroxide; In dimethyl sulfoxide; at 130 ℃; for 3h;
DOI:10.1021/ja029957n

Reference yield:

: 70887-29-5
4-methoxybenzyl iodide

: 545374-96-7
(2S,4aR,8aR)-cis-2-[8-(4-methoxy-benzyloxymethyl)-4a-methyl-1,2,4a,8a-tetrahydronaphthalen-2-yl]-propionic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 0.25 h / -60 °C

1.2: dimethylformamide / 3 h / -50 °C

2.1: 95 percent / DMAP; pyridine / CH₂Cl₂ / 15 h / 0 °C

3.1: 99 percent / [Pd[ethane-1,2-diylbis(diphenylphosphine)]2] / various solvent(s) / 24 h / 20 °C

4.1: 93 percent / aq. NaOH / dimethylsulfoxide / 4 h / 130 °C

With pyridine; dmap; sodium hydroxide; bis(bis(1,2-diphenylphosphino)ethane)palladium⁽⁰⁾; sodium hydride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1002/hlca.200590078

Reference yield:

: 862207-41-8
(4aR,8aS)-cis-4a-methyl-5-oxo-4a,5,8,8a-tetrahydro-naphthalene-1-carbaldehyde

: 545374-96-7
(2S,4aR,8aR)-cis-2-[8-(4-methoxy-benzyloxymethyl)-4a-methyl-1,2,4a,8a-tetrahydronaphthalen-2-yl]-propionic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: CeCl₃*7H₂O; NaBH₄ / methanol / 1.5 h / 0 °C

2.1: NaH / dimethylformamide / 0.25 h / -60 °C

2.2: dimethylformamide / 3 h / -50 °C

3.1: 95 percent / DMAP; pyridine / CH₂Cl₂ / 15 h / 0 °C

4.1: 99 percent / [Pd[ethane-1,2-diylbis(diphenylphosphine)]2] / various solvent(s) / 24 h / 20 °C

5.1: 93 percent / aq. NaOH / dimethylsulfoxide / 4 h / 130 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; bis(bis(1,2-diphenylphosphino)ethane)palladium⁽⁰⁾; sodium hydride; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1002/hlca.200590078