(S)-5-(benzyloxymethyl)-3-[2-methoxy-3-(2-naphthylmethoxy)propoxy]-2-methylpyridine-4-carbaldehyde

Base Information

Chemical Name:(S)-5-(benzyloxymethyl)-3-[2-methoxy-3-(2-naphthylmethoxy)propoxy]-2-methylpyridine-4-carbaldehyde
CAS No.:252272-62-1
Molecular Formula:C₃₀H₃₁NO₅
Molecular Weight:485.58
Hs Code.:

Synonyms:(S)-5-(benzyloxymethyl)-3-[2-methoxy-3-(2-naphthylmethoxy)propoxy]-2-methylpyridine-4-carbaldehyde

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Chemical Property of (S)-5-(benzyloxymethyl)-3-[2-methoxy-3-(2-naphthylmethoxy)propoxy]-2-methylpyridine-4-carbaldehyde

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Technology Process of (S)-5-(benzyloxymethyl)-3-[2-methoxy-3-(2-naphthylmethoxy)propoxy]-2-methylpyridine-4-carbaldehyde

There total 6 articles about (S)-5-(benzyloxymethyl)-3-[2-methoxy-3-(2-naphthylmethoxy)propoxy]-2-methylpyridine-4-carbaldehyde 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%

: 252272-52-9
(S)-5-(benzyloxymethyl)-3-[2-methoxy-3-(2-naphthylmethoxy)propoxy]-2-methylpyridine-4-carbaldehyde dimethyl acetal

: 252272-62-1
(S)-5-(benzyloxymethyl)-3-[2-methoxy-3-(2-naphthylmethoxy)propoxy]-2-methylpyridine-4-carbaldehyde

Guidance literature:: With acetic acid; Heating;
DOI:10.1039/CC9960001073

Reference yield:

: 1592-38-7
2-Naphthalenemethanol

: 252272-62-1
(S)-5-(benzyloxymethyl)-3-[2-methoxy-3-(2-naphthylmethoxy)propoxy]-2-methylpyridine-4-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: 74 percent / tropylium tetrafluoroborate / 3 h / 70 °C

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: 97 percent / 4 h / 20 °C

3.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 10 h / 20 °C

4.1: 76 percent / triphenylphosphine, NBS / CH₂Cl₂ / 0.08 h / 20 °C

5.1: NaH / dimethylformamide / 1 h / 20 °C

5.2: 72 percent / dimethylformamide / 4 h / 80 °C

6.1: 87 percent / aq. AcOH / 12 h / 100 °C

With N-Bromosuccinimide; tetrabutyl ammonium fluoride; tropylium tetrafluoroborate; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Addition / 2.1: Metallation / 2.2: Substitution / 3.1: Substitution / 4.1: Bromination / 5.1: Metallation / 5.2: Substitution / 6.1: Hydrolysis;
DOI:10.1016/S0040-4020(99)00708-5

Reference yield:

: 105-36-2
ethyl bromoacetate

: (S)-2-{[1-{5-Benzyloxymethyl-3-[(S)-2-methoxy-3-(naphthalen-2-ylmethoxy)-propoxy]-2-methyl-pyridin-4-yl}-meth-(E)-ylidene]-amino}-propionic acid benzyl ester

: 252272-62-1
(S)-5-(benzyloxymethyl)-3-[2-methoxy-3-(2-naphthylmethoxy)propoxy]-2-methylpyridine-4-carbaldehyde

: (R)-2-Amino-2-methyl-succinic acid 1-benzyl ester 4-ethyl ester

: (S)-2-Amino-2-methyl-succinic acid 1-benzyl ester 4-ethyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at -78 ℃; for 10h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4020(99)00708-5