(E)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

Base Information

Chemical Name:(E)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one
CAS No.:228120-04-5
Molecular Formula:C₃₃H₃₂N₂O₉S
Molecular Weight:632.691
Hs Code.:

Synonyms:(E)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

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Chemical Property of (E)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

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Technology Process of (E)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

There total 1 articles about (E)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-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: 61.0%

: 115491-93-5
diallyl dicarbonate

: 560130-29-2
4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

: 228120-04-5
(E)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

: (Z)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

Guidance literature:: With dmap; In tetrahydrofuran; at 20 ℃; for 0.166667h;
DOI:10.1016/S0040-4020(03)00378-8

Reference yield: 75.0%

: 161150-59-0
(3R)-3-amino-4-(t-butyldiphenylsilyl)oxy-2-butanone dimethyl acetal

: 228120-04-5
(E)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

: 161150-62-5
(3R,4R,5S)-2-[(E)-1-benzoylamino-1-[1-(t-butyldiphenylsiloxy)methyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

: 161275-55-4
(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[1-(t-butyldiphenylsiloxy)methyl-2,2-dimethoxypropyl]-carbamoyl]methylidene-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

Guidance literature:: With dmap; In toluene; at 50 ℃; for 2h;
DOI:10.1016/S0040-4020(03)00378-8

Reference yield:

: 228120-04-5
(E)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

: (3R,4R,5S)-2-[(E)-1-benzoylamino-1-((4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-1-azabicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / DMAP / toluene / 2 h / 50 °C

2: 93 percent / HF-pyridine complex / pyridine / 1.5 h / 0 - 20 °C

3: 68 percent / PDC; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

4: p-TsOH*H₂O / tetrahydrofuran / 0.5 h / 20 °C

5: 5.7 mg / diethyl ether; tetrahydrofuran / 12 h / 20 °C

6: 57 percent / Ph₃P; AcOH; Pd(PPh₃)4 / tetrahydrofuran / 0.17 h / 20 °C

7: 73 percent / tetrabutylammonium fluoride; molecular sieves 4 Angstroem / tetrahydrofuran / 0.17 h / 20 °C

With dmap; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4 A molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; triphenylphosphine; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; toluene;
DOI:10.1016/S0040-4020(03)00378-8