(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

Base Information

Chemical Name:(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
CAS No.:1214271-04-1
Molecular Formula:C₃₉H₄₃NO₇
Molecular Weight:637.773
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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: 100.0%

: 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

: 100-39-0
benzyl bromide

: 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

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃;
DOI:10.1039/b918233k

Reference yield:

: C₂₆H₃₈O₉

: 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

Guidance literature:: Multi-step reaction with 5 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

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; In tetrahydrofuran; dichloromethane; water; acetone; 1.1: |Petasis Reaction;
DOI:10.1021/jo5005923

Reference yield:

: 4-(4-methoxybenzyloxy)pentane-1,2-diol

: 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

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; potassium bromide; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 °C

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

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

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

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

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

6.2: 18 h / 0 - 18 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium osmate(VI) dihydrate; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; potassium bromide; In tetrahydrofuran; dichloromethane; water; acetone; 2.1: |Petasis Reaction;
DOI:10.1021/jo5005923