(2R,4S,5R)-4-(benzyloxy)-N-methoxy-N-methyl-5-vinyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]-oxazine]-6'-carboxamide

Base Information

Chemical Name:(2R,4S,5R)-4-(benzyloxy)-N-methoxy-N-methyl-5-vinyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]-oxazine]-6'-carboxamide
CAS No.:1401113-04-9
Molecular Formula:C₂₂H₂₆N₂O₅
Molecular Weight:398.459
Hs Code.:

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Chemical Property of (2R,4S,5R)-4-(benzyloxy)-N-methoxy-N-methyl-5-vinyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]-oxazine]-6'-carboxamide

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Technology Process of (2R,4S,5R)-4-(benzyloxy)-N-methoxy-N-methyl-5-vinyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]-oxazine]-6'-carboxamide

There total 11 articles about (2R,4S,5R)-4-(benzyloxy)-N-methoxy-N-methyl-5-vinyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]-oxazine]-6'-carboxamide 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:

: 1401113-05-0
C₂₃H₃₀N₂O₆

: 1401113-04-9
(2R,4S,5R)-4-(benzyloxy)-N-methoxy-N-methyl-5-vinyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]-oxazine]-6'-carboxamide

: 1401113-17-4
(2S,4S,5R)-4-(benzyloxy)-N-methoxy-N-methyl-5-vinyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]-oxazine]-6'-carboxamide

Guidance literature:: With bis(benzonitrile)palladium(II) dichloride; In dichloromethane; at 0 ℃; for 12h; Overall yield = 87 %; Inert atmosphere; Molecular sieve;
DOI:10.1021/jo301835e

Reference yield:

: 1401113-06-1
5-formyl-N-methoxy-N-methyl-1H-pyrrole-2-carboxamide

: 1401113-04-9
(2R,4S,5R)-4-(benzyloxy)-N-methoxy-N-methyl-5-vinyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]-oxazine]-6'-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1: caesium carbonate / acetonitrile / 8.5 h / 0 °C / Inert atmosphere

2: lithium tris(3-ethyl-3-pentoyloxy)aluminohydride / tetrahydrofuran / 2.5 h / 0 °C / Inert atmosphere

3: bis(benzonitrile)palladium(II) dichloride / dichloromethane / 12 h / 0 °C / Inert atmosphere; Molecular sieve

With bis(benzonitrile)palladium(II) dichloride; lithium tris(3-ethyl-3-pentoyloxy)aluminohydride; caesium carbonate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo301835e

Reference yield:

: (R,E)-ethyl-4-(benzyloxy)-5-hydroxypent-2-enoate

: 1401113-04-9
(2R,4S,5R)-4-(benzyloxy)-N-methoxy-N-methyl-5-vinyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]-oxazine]-6'-carboxamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.5 h / 45 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 0.75 h / 0 °C / Inert atmosphere

3.1: sodium hydride; tert-butyl alcohol / N,N-dimethyl-formamide / 0.92 h / 0 °C

3.2: 5 h / 0 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 °C / Inert atmosphere

5.1: bis-[(trifluoroacetoxy)iodo]benzene / tetrahydrofuran; methanol; water / 0.75 h / 0 °C / Inert atmosphere

6.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / Inert atmosphere

7.1: caesium carbonate / acetonitrile / 8.5 h / 0 °C / Inert atmosphere

8.1: lithium tris(3-ethyl-3-pentoyloxy)aluminohydride / tetrahydrofuran / 2.5 h / 0 °C / Inert atmosphere

9.1: bis(benzonitrile)palladium(II) dichloride / dichloromethane / 12 h / 0 °C / Inert atmosphere; Molecular sieve

With lithium aluminium tetrahydride; bis(benzonitrile)palladium(II) dichloride; carbon tetrabromide; lithium tris(3-ethyl-3-pentoyloxy)aluminohydride; sodium hydride; caesium carbonate; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo301835e