ethyl (2E,4R)-7-((R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl)-4-(tert-butyldimethylsilyloxy)-7-oxohept-2-enoate

Base Information

Chemical Name:ethyl (2E,4R)-7-((R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl)-4-(tert-butyldimethylsilyloxy)-7-oxohept-2-enoate
CAS No.:866138-78-5
Molecular Formula:C₂₅H₃₇NO₆Si
Molecular Weight:475.657
Hs Code.:

Synonyms:ethyl (2E,4R)-7-((R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl)-4-(tert-butyldimethylsilyloxy)-7-oxohept-2-enoate

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Chemical Property of ethyl (2E,4R)-7-((R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl)-4-(tert-butyldimethylsilyloxy)-7-oxohept-2-enoate

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Technology Process of ethyl (2E,4R)-7-((R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl)-4-(tert-butyldimethylsilyloxy)-7-oxohept-2-enoate

There total 9 articles about ethyl (2E,4R)-7-((R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl)-4-(tert-butyldimethylsilyloxy)-7-oxohept-2-enoate 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%

: 866138-91-2
(R)-5-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-(tert-butyl-dimethyl-silanyloxy)-5-oxo-pentanal

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 866138-78-5
ethyl (2E,4R)-7-((R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl)-4-(tert-butyldimethylsilyloxy)-7-oxohept-2-enoate

Guidance literature:: With n-butyllithium; In 1,2-dimethoxyethane; hexane; at 20 ℃; for 5h;
DOI:10.1021/ol051200o

Reference yield:

: (R)-4-hydroxy-5-(4-methoxybenzyloxy)pentanoic acid

: 866138-78-5
ethyl (2E,4R)-7-((R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl)-4-(tert-butyldimethylsilyloxy)-7-oxohept-2-enoate

Guidance literature:: Multi-step reaction with 7 steps

1: imidazole / CH₂Cl₂ / 5 h / 20 °C

2: 6.6 g / aq. K₂CO₃ / methanol; tetrahydrofuran / 1 h / 0 °C

3: Et₃N / tetrahydrofuran / 3 h / 0 °C

4: 6.7 g / BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

5: 93 percent / DDQ; H₂O / CH₂Cl₂ / 0 - 20 °C

6: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7: 90 percent / BuLi / 1,2-dimethoxy-ethane; hexane / 5 h / 20 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; water; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; 6: Swern oxidation / 7: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol051200o

Reference yield:

: 866138-76-3
(R)-4-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pentanoic acid

: 866138-78-5
ethyl (2E,4R)-7-((R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl)-4-(tert-butyldimethylsilyloxy)-7-oxohept-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 3 h / 0 °C

2: 6.7 g / BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

3: 93 percent / DDQ; H₂O / CH₂Cl₂ / 0 - 20 °C

4: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 90 percent / BuLi / 1,2-dimethoxy-ethane; hexane / 5 h / 20 °C

With n-butyllithium; oxalyl dichloride; water; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; 4: Swern oxidation / 5: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol051200o