(2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

Base Information

Chemical Name:(2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
CAS No.:1401113-19-6
Molecular Formula:C₁₉H₂₁NO₅
Molecular Weight:343.379
Hs Code.:

Synonyms:(2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

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Chemical Property of (2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

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Technology Process of (2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

There total 14 articles about (2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde 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: 84.0%

: 1401113-18-5
(2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-N-methoxy-Nmethyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c]-[1,4]oxazine]-6′-carboxamide

: 1401113-19-6
(2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - 0 ℃; for 1.5h;
DOI:10.1021/jo301835e

Reference yield:

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

: 1401113-19-6
(2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

Guidance literature:: Multi-step reaction with 12 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

10.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water / 24 h / Inert atmosphere

11.1: sodium periodate / tetrahydrofuran / 12 h / 0 °C / pH 7 / Inert atmosphere

11.2: 1 h / 0 °C / Inert atmosphere

12.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -78 - 0 °C

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; bis(benzonitrile)palladium(II) dichloride; carbon tetrabromide; lithium tris(3-ethyl-3-pentoyloxy)aluminohydride; sodium hydride; caesium carbonate; 4-methylmorpholine N-oxide; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo301835e

Reference yield:

: 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

: 1401113-19-6
(2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water / 24 h / Inert atmosphere

2.1: sodium periodate / tetrahydrofuran / 12 h / 0 °C / pH 7 / Inert atmosphere

2.2: 1 h / 0 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -78 - 0 °C

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water;
DOI:10.1021/jo301835e