(R)-1-((1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-oxohexahydropyrrolo[1,2-c]oxazol-1-yl)propan-2-yl 4-nitrobenzoate

Base Information

Chemical Name:(R)-1-((1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-oxohexahydropyrrolo[1,2-c]oxazol-1-yl)propan-2-yl 4-nitrobenzoate
CAS No.:1609017-72-2
Molecular Formula:C₃₈H₃₈N₂O₉
Molecular Weight:666.728
Hs Code.:

Synonyms:(R)-1-((1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-oxohexahydropyrrolo[1,2-c]oxazol-1-yl)propan-2-yl 4-nitrobenzoate

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Chemical Property of (R)-1-((1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-oxohexahydropyrrolo[1,2-c]oxazol-1-yl)propan-2-yl 4-nitrobenzoate

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Technology Process of (R)-1-((1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-oxohexahydropyrrolo[1,2-c]oxazol-1-yl)propan-2-yl 4-nitrobenzoate

There total 8 articles about (R)-1-((1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-oxohexahydropyrrolo[1,2-c]oxazol-1-yl)propan-2-yl 4-nitrobenzoate 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: 85.0%

: 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

: 62-23-7
4-nitro-benzoic acid

: 1609017-72-2
(R)-1-((1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-oxohexahydropyrrolo[1,2-c]oxazol-1-yl)propan-2-yl 4-nitrobenzoate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 0 - 27 ℃; for 24h;
DOI:10.1021/jo5005923

Reference yield:

: 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

: 1609017-72-2
(R)-1-((1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-oxohexahydropyrrolo[1,2-c]oxazol-1-yl)propan-2-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 4 h / 26 °C

2: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 24 h / 0 - 27 °C

With di-isopropyl azodicarboxylate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; toluene; 2: |Mitsunobu Displacement;
DOI:10.1021/jo5005923

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

: 1609017-72-2
(R)-1-((1R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-oxohexahydropyrrolo[1,2-c]oxazol-1-yl)propan-2-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 3 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

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 24 h / 0 - 27 °C

With di-isopropyl azodicarboxylate; tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene; 3.1: |Mitsunobu Displacement;
DOI:10.1021/jo5005923