(2S,4aR,5S)-5-(benzyloxy)-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]-oxazin-8(2H)-one

Base Information

Chemical Name:(2S,4aR,5S)-5-(benzyloxy)-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]-oxazin-8(2H)-one
CAS No.:303191-02-8
Molecular Formula:C₁₉H₂₇NO₅
Molecular Weight:349.427
Hs Code.:

Synonyms:(2S,4aR,5S)-5-(benzyloxy)-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]-oxazin-8(2H)-one

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Chemical Property of (2S,4aR,5S)-5-(benzyloxy)-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]-oxazin-8(2H)-one

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Technology Process of (2S,4aR,5S)-5-(benzyloxy)-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]-oxazin-8(2H)-one

There total 12 articles about (2S,4aR,5S)-5-(benzyloxy)-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]-oxazin-8(2H)-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: 99.0%

: 303191-00-6
(2R,4aR,5S)-5-(benzyloxy)-2-[-(methoxymethoxy)ethyl]-4a,5,6,7-tetrahydropyrido[1,2-b][1,2]oxazin-8(2H)-one

: 303191-02-8
(2S,4aR,5S)-5-(benzyloxy)-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]-oxazin-8(2H)-one

Guidance literature:: With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 0.5h;
DOI:10.1021/jo001589n

Reference yield:

: 164577-87-1
ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-enoate

: 303191-02-8
(2S,4aR,5S)-5-(benzyloxy)-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]-oxazin-8(2H)-one

Guidance literature:: Multi-step reaction with 12 steps

1: 97 percent / DIBAL-H / tetrahydrofuran; hexane / 0.5 h / 20 °C

2: 85 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

3: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

4: 98 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / Heating

5: 99 percent / DIBAL-H / CH₂Cl₂; hexane / 4 h / 0 °C

6: 90 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 3 h / 0 °C

7: 91 percent / dimethylsulfoxide / 1 h / 50 °C

8: NaOH / H₂O / 4 h / Heating

9: 86 percent / diethyl ether / 0.5 h / 0 °C

10: 80 percent / hydroxylamine hydrochloride; KOH / methanol / 1 h / 0 °C

11: solid tetrapropylammonium (meta)periodate / H₂O; dimethylformamide / 0.5 h / 0 °C

12: 99 percent / H₂ / Pd/C / tetrahydrofuran / 0.5 h

With dmap; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; tetrapropylammonium periodate; hydroxylamine hydrochloride; hydrogen; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 11: intramolecular Diels-Alder reaction;
DOI:10.1021/jo001589n

Reference yield:

: 164471-44-7
ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-en-ol

: 303191-02-8
(2S,4aR,5S)-5-(benzyloxy)-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]-oxazin-8(2H)-one

Guidance literature:: Multi-step reaction with 11 steps

1: 85 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

2: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

3: 98 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / Heating

4: 99 percent / DIBAL-H / CH₂Cl₂; hexane / 4 h / 0 °C

5: 90 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 3 h / 0 °C

6: 91 percent / dimethylsulfoxide / 1 h / 50 °C

7: NaOH / H₂O / 4 h / Heating

8: 86 percent / diethyl ether / 0.5 h / 0 °C

9: 80 percent / hydroxylamine hydrochloride; KOH / methanol / 1 h / 0 °C

10: solid tetrapropylammonium (meta)periodate / H₂O; dimethylformamide / 0.5 h / 0 °C

11: 99 percent / H₂ / Pd/C / tetrahydrofuran / 0.5 h

With dmap; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; tetrapropylammonium periodate; hydroxylamine hydrochloride; hydrogen; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 10: intramolecular Diels-Alder reaction;
DOI:10.1021/jo001589n