(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Base Information

• Chemical Name: (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
• CAS No.: 100101-49-3
• Molecular Formula: C₃₀H₃₃N₃O₆
• Molecular Weight: 531.609
• Mol file: 100101-49-3.mol

Synonyms:

Chemical Property of (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

There total 6 articles about (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester 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:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester (100101-49-3)

Guidance literature:

Multi-step reaction with 5 steps

1: O₂, thiourea, sodium acetate, Rose bengal / methanol / 9 h / -5 °C / Irradiation

2: 62 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 48 h / Ambient temperature

3: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C

4: 92 percent / 75percent aq. HClO₄ / acetone / 1 h / Ambient temperature

5: pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; dmap; sodium azide; perchloric acid; oxygen; sodium acetate; rose bengal; thiourea; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00358a023

Reference yield:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) → (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester (100101-49-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 48 h / Ambient temperature

2: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C

3: 92 percent / 75percent aq. HClO₄ / acetone / 1 h / Ambient temperature

4: pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; dmap; sodium azide; perchloric acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00358a023

Reference yield:

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) → (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester (100101-49-3)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / benzene; dimethylformamide / 1 h / Ambient temperature

2: pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; dmap; oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00358a023

upstream raw materials:

(S)-naproxenoyl chloride

(+/-)-(1α,2β,3α,4α,5β)-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol

5-(benzyloxymethyl)cyclopentadiene

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

Refernces