(3S,5S,6R)-4(benzyloxycarbonyl)-3-(2'-cyclopentenyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Base Information

Chemical Name:(3S,5S,6R)-4(benzyloxycarbonyl)-3-(2'-cyclopentenyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
CAS No.:112741-61-4
Molecular Formula:C₂₉H₂₇NO₄
Molecular Weight:453.538
Hs Code.:

Synonyms:(3S,5S,6R)-4(benzyloxycarbonyl)-3-(2'-cyclopentenyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

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Chemical Property of (3S,5S,6R)-4(benzyloxycarbonyl)-3-(2'-cyclopentenyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

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Technology Process of (3S,5S,6R)-4(benzyloxycarbonyl)-3-(2'-cyclopentenyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

There total 5 articles about (3S,5S,6R)-4(benzyloxycarbonyl)-3-(2'-cyclopentenyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-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:

: 14579-08-9
3-trimethylsilylcyclopent-1-ene

: 111934-06-6
(3S,5S,6R)-4-(benzyloxycarbonyl)-3-bromo-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

: 112741-62-5
(3S,5S,6R)-3-(R)-Cyclopent-2-enyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

: 112741-61-4
(3S,5S,6R)-4(benzyloxycarbonyl)-3-(2'-cyclopentenyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Guidance literature:: With zinc(II) chloride; In tetrahydrofuran; at 25 ℃; for 15h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1021/ja00213a031

Reference yield:

: 23190-16-1
(1R,2S)-2-Amino-1,2-diphenylethanol

: 112741-61-4
(3S,5S,6R)-4(benzyloxycarbonyl)-3-(2'-cyclopentenyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 84.3 percent / triethylamine / tetrahydrofuran / 18 h

2: 9.6 g / NaHCO₃ / CH₂Cl₂; H₂O / 12 h

3: 77.9 percent / p-toluenesulfonic acid monohydrate, CaCl₂ / benzene / 8 h / Heating

4: 100 percent / N-bromosuccinimide / CCl₄ / 0.75 h / Heating

5: ZnCl₂ / tetrahydrofuran / 15 h / 25 °C

With N-Bromosuccinimide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; calcium chloride; zinc(II) chloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; benzene;
DOI:10.1021/ja00213a031

Reference yield:

: 100516-54-9,335159-14-3
(5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

: 112741-61-4
(3S,5S,6R)-4(benzyloxycarbonyl)-3-(2'-cyclopentenyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / N-bromosuccinimide / CCl₄ / 0.75 h / Heating

2: ZnCl₂ / tetrahydrofuran / 15 h / 25 °C

With N-Bromosuccinimide; zinc(II) chloride; In tetrahydrofuran; tetrachloromethane;
DOI:10.1021/ja00213a031