(4S)-4-(4'-benzyloxy)benzyl-4,5-dihydrooxazoline

Base Information

• Chemical Name: (4S)-4-(4'-benzyloxy)benzyl-4,5-dihydrooxazoline
• CAS No.: 132376-98-8
• Molecular Formula: C₁₇H₁₇NO₂
• Molecular Weight: 267.327
• Mol file: 132376-98-8.mol

Synonyms:(4S)-4-(4'-benzyloxy)benzyl-4,5-dihydrooxazoline

Chemical Property of (4S)-4-(4'-benzyloxy)benzyl-4,5-dihydrooxazoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (4S)-4-(4'-benzyloxy)benzyl-4,5-dihydrooxazoline

There total 4 articles about (4S)-4-(4'-benzyloxy)benzyl-4,5-dihydrooxazoline 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: 80.0%

(S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol (85803-44-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → (4S)-4-(4'-benzyloxy)benzyl-4,5-dihydrooxazoline (132376-98-8)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 48h; Inert atmosphere; Reflux;

DOI:10.1139/V10-162

Reference yield:

ethyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-O-(phenylmethyl)-L-tyrosinate (127132-32-5) → (4S)-4-(4'-benzyloxy)benzyl-4,5-dihydrooxazoline (132376-98-8)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

2: acetyl chloride / methanol; ethyl acetate / 24.5 h / 0 - 20 °C

3: toluene-4-sulfonic acid / toluene / 48 h / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; toluene-4-sulfonic acid; acetyl chloride; In tetrahydrofuran; methanol; ethyl acetate; toluene;

DOI:10.1139/V10-162

Reference yield:

benzyl bromide (100-39-0) → (4S)-4-(4'-benzyloxy)benzyl-4,5-dihydrooxazoline (132376-98-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 18-crown-6 ether; potassium carbonate / N,N-dimethyl-formamide / 24 h / 40 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

3: acetyl chloride / methanol; ethyl acetate / 24.5 h / 0 - 20 °C

4: toluene-4-sulfonic acid / toluene / 48 h / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; 18-crown-6 ether; potassium carbonate; toluene-4-sulfonic acid; acetyl chloride; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1139/V10-162

upstream raw materials:

(S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol

N,N-dimethyl-formamide dimethyl acetal

N-(tert-butoxycarbonyl)-L-tyrosine ethyl ester

ethyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-O-(phenylmethyl)-L-tyrosinate

Downstream raw materials:

(4S)-4-(4'-p-hydroxy)benzyl-4,5-dihydrooxazoline