5-Methyl-naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester

Base Information

• Chemical Name: 5-Methyl-naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester
• CAS No.: 783323-30-8
• Molecular Formula: C₂₄H₂₂O₅
• Molecular Weight: 390.436
• Mol file: 783323-30-8.mol

Synonyms:5-Methyl-naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester

Chemical Property of 5-Methyl-naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Methyl-naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester

There total 5 articles about 5-Methyl-naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl 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:

(S)-benzyl 2-hydroxy-2-((S)-2-methyloxiran-2-yl)acetate (127661-25-0) + 5-methyl-naphthalene-1-carbonyl chloride (101665-68-3) → 5-Methyl-naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester (783323-30-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1021/ol048653y

Reference yield:

5-methyl-1-naphthoic acid (4527-60-0) → 5-Methyl-naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester (783323-30-8)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMF / CH₂Cl₂ / 4 h

2: Et₃N; DMAP / CH₂Cl₂ / 4 h / 0 °C

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

DOI:10.1021/ol048653y

Reference yield:

3-hydroxy-5-methylnaphthalene-1-carboxylic acid ethyl ester (86535-58-2) → 5-Methyl-naphthalene-1-carboxylic acid (S)-benzyloxycarbonyl-((S)-2-methyl-oxiranyl)-methyl ester (783323-30-8)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂

2: Et₃SiH; Pd(dppf)Cl₂ / dimethylformamide / 60 °C

3: aq. LiOH / methanol

4: (COCl)2; DMF / CH₂Cl₂ / 4 h

5: Et₃N; DMAP / CH₂Cl₂ / 4 h / 0 °C

With triethylsilane; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol048653y

upstream raw materials:

(S)-benzyl 2-hydroxy-2-((S)-2-methyloxiran-2-yl)acetate

5-methyl-naphthalene-1-carbonyl chloride

5-methyl-1-naphthoic acid

3-hydroxy-5-methylnaphthalene-1-carboxylic acid ethyl ester