Propanedioic acid, diazo-, (2S)-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-ethylpentyl methyl ester

Base Information

• Chemical Name: Propanedioic acid, diazo-, (2S)-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-ethylpentyl methyl ester
• CAS No.: 262846-97-9
• Molecular Formula: C27H36N2O5Si
• Molecular Weight: 496.679
• Mol file: 262846-97-9.mol

Synonyms:

Chemical Property of Propanedioic acid, diazo-, (2S)-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-ethylpentyl methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Propanedioic acid, diazo-, (2S)-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-ethylpentyl methyl ester

There total 9 articles about Propanedioic acid, diazo-, (2S)-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-ethylpentyl 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: 88.0%

(2S)-[5-(t-butyldiphenylsilyloxy)-2-ethylpentyl]-α-(methoxycarbonyl)acetate (262847-00-7) → (2S)-[5-(tert-butyldiphenylsilyloxy)-2-ethylpentyl]-α-diazo-α-(methoxycarbonyl)acetate (262846-97-9)

Guidance literature:

With triethylamine; Methanesulfonyl azide; In acetonitrile;

DOI:10.1016/S0040-4039(99)02131-0

Reference yield:

(4R,5S)-3-[(2S)-1-oxo-2-ethyl-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone (121074-25-7,121074-20-2) → (2S)-[5-(tert-butyldiphenylsilyloxy)-2-ethylpentyl]-α-diazo-α-(methoxycarbonyl)acetate (262846-97-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 50 percent / LiAlH₄ / -5 °C

2.1: 86 percent / DCC; DMAP / CH₂Cl₂ / 1 h / 0 °C

3.1: disiamylborane / tetrahydrofuran / 0 - 20 °C

3.2: 74 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.33 h / 10 - 20 °C

4.1: 89 percent / pyridine / 12 h / 0 - 20 °C

5.1: 88 percent / MsN₃; Et₃N / acetonitrile / 10 h / 20 °C

With pyridine; dmap; lithium aluminium tetrahydride; bis-(1,2-dimethylpropyl)borane; triethylamine; Methanesulfonyl azide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo010751z

Reference yield:

(4R,5S)-3[(2R)-2-((1R*)-1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone (393563-08-1) → (2S)-[5-(tert-butyldiphenylsilyloxy)-2-ethylpentyl]-α-diazo-α-(methoxycarbonyl)acetate (262846-97-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 92 percent / DMAP; pyridine / CH₂Cl₂ / 3 h / 20 °C

2.1: 76 percent / Bu₃SnH; AIBN / toluene / 12 h / 75 °C

3.1: 100 percent / LiOH*H₂O; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

4.1: 0.023 g / LiAlH₄ / diethyl ether / 0 - 20 °C

5.1: 86 percent / DCC; DMAP / CH₂Cl₂ / 1 h / 0 °C

6.1: disiamylborane / tetrahydrofuran / 0 - 20 °C

6.2: 74 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.33 h / 10 - 20 °C

7.1: 89 percent / pyridine / 12 h / 0 - 20 °C

8.1: 88 percent / MsN₃; Et₃N / acetonitrile / 10 h / 20 °C

With pyridine; dmap; lithium hydroxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; bis-(1,2-dimethylpropyl)borane; triethylamine; Methanesulfonyl azide; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo010751z

upstream raw materials:

(2S)-[5-(t-butyldiphenylsilyloxy)-2-ethylpentyl]-α-(methoxycarbonyl)acetate

(4R,5S)-3-[(2S)-1-oxo-2-ethyl-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone

(4R,5S)-3[(2R)-2-((1R*)-1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone

(4R,5S)-3-[(2R)-2((1R*)-1-(phenoxythiocarbonyloxy)ethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone

Downstream raw materials:

(1S,12bR)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine

(1S,12bS)-1-ethyl-1-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine

(5S)-N-[2-(3-indolyl)ethyl]-5-ethyl-5-(2-tert-butyldiphenylsiloxyethyl)-6-hydroxy-δ-lactam

(4S)-N-[2-(3-indolyl)-ethyl]-4-ethyl-4-hydroxymethyl-6-tert-butyldiphenylsiloxyhexamide