3-Furancarboxylic acid, 4-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-ethyltetrahydro-2-oxo -, methyl ester, (4S)-

Base Information

• Chemical Name: 3-Furancarboxylic acid, 4-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-ethyltetrahydro-2-oxo -, methyl ester, (4S)-
• CAS No.: 262847-01-8
• Molecular Formula: C27H36O5Si
• Molecular Weight: 468.665
• Mol file: 262847-01-8.mol

Synonyms:

Chemical Property of 3-Furancarboxylic acid, 4-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-ethyltetrahydro-2-oxo -, methyl ester, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Furancarboxylic acid, 4-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-ethyltetrahydro-2-oxo -, methyl ester, (4S)-

There total 11 articles about 3-Furancarboxylic acid, 4-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-4-ethyltetrahydro-2-oxo -, methyl ester, (4S)- 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: 90.0%

(2S)-[5-(tert-butyldiphenylsilyloxy)-2-ethylpentyl]-α-diazo-α-(methoxycarbonyl)acetate (262846-97-9) → (4S)-4-[3-(tert-butyldiphenylsilyloxypropyl)]-4-ethyl-3-(methoxycarbonyl)dihydro-2(3H)-furanone (262847-01-8)

Guidance literature:

dirhodium tetraacetate; In dichloromethane; Heating;

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

Reference yield: 87.0%

(2S)-[5-(tert-butyldiphenylsilyloxy)-2-ethylpentyl]-α-diazo-α-(methoxycarbonyl)acetate (262846-97-9) → (4S)-4-[3-(tert-butyldiphenylsilyloxypropyl)]-4-ethyl-3-(methoxycarbonyl)dihydro-2(3H)-furanone (262847-01-8) + 2-[4-(tert-butyl-diphenyl-silanyloxy)-1-ethyl-butyl]-4-oxo-oxetane-3-carboxylic acid methyl ester

Guidance literature:

dirhodium tetraacetate; In dichloromethane; for 14h; Heating;

DOI:10.1021/jo010751z

Reference yield:

(4R,5S)-3-[(2S)-1-oxo-2-ethyl-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone (121074-25-7,121074-20-2) → (4S)-4-[3-(tert-butyldiphenylsilyloxypropyl)]-4-ethyl-3-(methoxycarbonyl)dihydro-2(3H)-furanone (262847-01-8)

Guidance literature:

Multi-step reaction with 6 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

6.1: 87 percent / Rh₂(OAc)4 / CH₂Cl₂ / 14 h / Heating

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

DOI:10.1021/jo010751z

upstream raw materials:

(2S)-[5-(tert-butyldiphenylsilyloxy)-2-ethylpentyl]-α-diazo-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