benzyl (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanoate

Base Information

• Chemical Name: benzyl (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanoate
• CAS No.: 127661-26-1
• Molecular Formula: C₂₅H₂₄O₆
• Molecular Weight: 420.462
• Mol file: 127661-26-1.mol

Synonyms:benzyl (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanoate

Chemical Property of benzyl (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanoate

There total 14 articles about benzyl (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanoate 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: 92.0%

C12H14O4 (937020-82-1) + 3-methoxy-5-methylnaphthalene-1-carboxylic acid (22250-90-4) → benzyl (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanoate (127661-26-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 25 ℃; for 4h;

DOI:10.1021/jo7014888

Reference yield: 88.0%

5-Methyl-3-methoxy-1-naphthoyl chloride (86535-59-3) + (S)-benzyl 2-hydroxy-2-((S)-2-methyloxiran-2-yl)acetate (127661-25-0) → benzyl (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanoate (127661-26-1)

Guidance literature:

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

DOI:10.1016/S1874-6004(04)80025-X

Reference yield:

3-methoxy-5-methylnaphthalene-1-carboxylic acid (22250-90-4) → benzyl (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanoate (127661-26-1)

Guidance literature:

Multi-step reaction with 2 steps

1: PCl₅

2: 88 percent / DMAP; Et₃N / CH₂Cl₂ / 4 h / 0 °C

With dmap; phosphorus pentachloride; triethylamine; In dichloromethane;

DOI:10.1016/S1874-6004(04)80025-X

upstream raw materials:

5-Methyl-3-methoxy-1-naphthoyl chloride

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

C₁₂H₁₄O₄

3-methoxy-5-methylnaphthalene-1-carboxylic acid

Downstream raw materials:

(S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-[(S)-2-(3-methoxy-5-methyl-naphthalene-1-carbonyloxy)-2-((S)-2-methyl-oxiranyl)-acetylamino]-4-(2-oxo-propylcarbamoyl)-1-triethylsilanyloxy-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

(S)-2-[(1R,2S)-2-Acetoxy-3-bromo-4-[(Z)-(S)-2-(3-methoxy-5-methyl-naphthalene-1-carbonyloxy)-2-((S)-2-methyl-oxiranyl)-acetylimino]-4-(2-oxo-propylcarbamoyl)-1-triethylsilanyloxy-butyl]-aziridine-1-carboxylic acid benzyl ester