(1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-hydroxypropyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

Base Information

Chemical Name:(1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-hydroxypropyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one
CAS No.:1214271-05-2
Molecular Formula:C₃₁H₃₅NO₆
Molecular Weight:517.622
Hs Code.:

Synonyms:(1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-hydroxypropyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

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Chemical Property of (1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-hydroxypropyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

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Technology Process of (1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-hydroxypropyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

There total 7 articles about (1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-hydroxypropyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-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: 89.0%

: 1214271-04-1
(1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-(4-methoxybenzyloxy)propyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

: 1214271-05-2
(1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-hydroxypropyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 4h; chemoselective reaction;
DOI:10.1039/b918233k

Reference yield:

: 1214271-02-9
(1R,5R,6R,7S,7aS)-5-(benzyloxymethyl)-6,7-dihydroxy-1-((S)-2-(4-methoxybenzyloxy)propyl)-tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

: 1214271-05-2
(1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-hydroxypropyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0.25 h / 18 °C / Inert atmosphere

1.2: 18 h / 0 - 18 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 4 h / 26 °C

With tetra-(n-butyl)ammonium iodide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo5005923

Reference yield:

: C₂₆H₃₈O₉

: 1214271-05-2
(1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1-((S)-2-hydroxypropyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: dichloromethane / 48 h / 32 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 18.25 h / 0 - 20 °C / Inert atmosphere

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / Inert atmosphere; Reflux

4.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 18 h / 35 °C

5.1: tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0.25 h / 18 °C / Inert atmosphere

5.2: 18 h / 0 - 18 °C / Inert atmosphere

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 4 h / 26 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium osmate(VI) dihydrate; tetra-(n-butyl)ammonium iodide; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetone; 1.1: |Petasis Reaction;
DOI:10.1021/jo5005923