4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxymethyl)pyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

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Chemical Name:4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxymethyl)pyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one
CAS No.:176298-13-8
Molecular Formula:C₃₄H₄₀N₂O₅Si
Molecular Weight:584.788
Hs Code.:

Synonyms:4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxymethyl)pyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

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Chemical Property of 4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxymethyl)pyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

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Technology Process of 4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxymethyl)pyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

There total 8 articles about 4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxymethyl)pyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one 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: 82.0%

: 1199-01-5,53766-22-6
2-phenylazlactone

: 161150-47-6
(2S,3R,4S)-3,4-dibenzyloxy-2-(t-butyldimethylsiloxy)methyl-5-methylthio-3,4-dihydro-2H-pyrrole

: 176298-13-8
4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxymethyl)pyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

Guidance literature:: In toluene; at 80 ℃;
DOI:10.1016/S0040-4039(00)78556-X DOI:10.1016/S0040-4020(03)00378-8

Reference yield:

: 60933-68-8
3,4,6-tri-O-benzyl-β-D-arabinofuranoside

: 176298-13-8
4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxymethyl)pyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: toluene / 12 h / Heating

2.1: 23.7 g / tetrahydrofuran / 12.5 h / 0 - 20 °C

3.1: 71 percent / PCC; molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h / 20 °C

4.1: O₃/O₂ / ethanol / 0.33 h / -25 °C

4.2: 98 percent / NaBH₄ / ethanol / 0.33 h / 20 °C

5.1: 99 percent / ammonium cerium (IV) nitrate / acetonitrile; H₂O / 1 h / 20 °C

6.1: 89 percent / imidazole / dimethylformamide / 1 h / 20 °C

7.1: 97 percent / Lawesson's reagent / toluene / 0.67 h / 60 °C

8.1: 97 percent / CH₂Cl₂ / 12 h / 20 °C

9.1: 82 percent / toluene / 80 °C

With Lawessons reagent; 1H-imidazole; ammonium cerium(IV) nitrate; 4 A molecular sieve; oxygen; ozone; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(03)00378-8

Reference yield:

: 157831-26-0
(3S,4R,5S)-3,4-dibenzyloxy-1-(4-methoxyphenylmethyl)-5-vinylpyrrolidin-2-one

: 176298-13-8
4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxymethyl)pyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: O₃/O₂ / ethanol / 0.33 h / -25 °C

1.2: 98 percent / NaBH₄ / ethanol / 0.33 h / 20 °C

2.1: 99 percent / ammonium cerium (IV) nitrate / acetonitrile; H₂O / 1 h / 20 °C

3.1: 89 percent / imidazole / dimethylformamide / 1 h / 20 °C

4.1: 97 percent / Lawesson's reagent / toluene / 0.67 h / 60 °C

5.1: 97 percent / CH₂Cl₂ / 12 h / 20 °C

6.1: 82 percent / toluene / 80 °C

With Lawessons reagent; 1H-imidazole; ammonium cerium(IV) nitrate; oxygen; ozone; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(03)00378-8