(4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one

Base Information

Chemical Name:(4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one
CAS No.:1443768-77-1
Molecular Formula:C₁₅H₁₅NO₄
Molecular Weight:273.288
Hs Code.:

Synonyms:(4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one

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Chemical Property of (4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one

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Technology Process of (4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one

There total 6 articles about (4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-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: 5.0%

: 1443768-72-6
(4S,5S)-N-benzyloxycarbonyl-4-vinyl-5-allyl-1,3-oxazinan-6-one

: 1443768-77-1
(4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 25 ℃; for 20h; Inert atmosphere;
DOI:10.1016/j.tet.2013.05.016

Reference yield:

: 1443768-72-6
(4S,5S)-N-benzyloxycarbonyl-4-vinyl-5-allyl-1,3-oxazinan-6-one

: 1443768-77-1
(4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one

: 1443769-13-8
benzyl (4aS,7aS) 4-oxo-4,4a,7,7a-tetrahydrocyclopenta[d][1,3]oxazine-1(2H)-carboxylate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; for 2h; Overall yield = 17 %; Inert atmosphere; Reflux;
DOI:10.1016/j.tet.2013.05.016

Reference yield:

: 3-([(benzyloxy)carbonyl]amino)-4-pentenoic acid

: 1443768-77-1
(4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: camphor-10-sulfonic acid / toluene / 90 °C / Molecular sieve; Inert atmosphere

2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.67 h / -78 °C / Inert atmosphere

2.2: -78 - -40 °C / Inert atmosphere

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 20 h / 25 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; camphor-10-sulfonic acid; potassium hexamethylsilazane; In tetrahydrofuran; toluene;
DOI:10.1016/j.tet.2013.05.016