dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate

Base Information

• Chemical Name: dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate
• CAS No.: 768395-80-8
• Molecular Formula: C₁₂H₂₄NO₇P
• Molecular Weight: 325.299
• Mol file: 768395-80-8.mol

Synonyms:dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate

Chemical Property of dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate

There total 1 articles about dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate 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: 48.0%

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate (40856-59-5,132957-40-5) + dimethyl methane phosphonate (756-79-6) → dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate (768395-80-8)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1021/jm040780c

Reference yield: 53.0%

tert-butyl glyoxylate (7633-32-1) + dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate (768395-80-8) → tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate (768395-82-0)

Guidance literature:

With triethylamine; lithium chloride; In acetonitrile; at 0 ℃; for 1h;

DOI:10.1021/jm040780c

Reference yield:

dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate (768395-80-8) → 3-amino-4-oxo-heptanedioic acid 1-benzyl ester (768395-72-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 53 percent / lithium chloride; triethylamine / acetonitrile / 1 h / 0 °C

2.1: 59 percent / H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

3.1: 62 percent / pyridinium dichromate / dimethylformamide / 2.5 h

4.1: aq. Cs₂CO₃ / methanol / pH 8

4.2: 72 percent / dimethylformamide / 6 h / 20 °C

5.1: 97 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

With dipyridinium dichromate; hydrogen; caesium carbonate; triethylamine; trifluoroacetic acid; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jm040780c

upstream raw materials:

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate

dimethyl methane phosphonate

Downstream raw materials:

tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate

3-amino-4-oxo-heptanedioic acid 1-benzyl ester

benzyl (3R/S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoate