(1R,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

Base Information

Chemical Name:(1R,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol
CAS No.:1214271-08-5
Molecular Formula:C₃₀H₃₅NO₄
Molecular Weight:473.612
Hs Code.:

Synonyms:(1R,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

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Chemical Property of (1R,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

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Technology Process of (1R,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

There total 10 articles about (1R,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol 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: 77.0%

: 1214271-16-5
(1R,3R)-1-((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-yl)butane-1,3-diol

: 1214271-08-5
(1R,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 1.5h; Inert atmosphere;
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

: 1214271-08-5
(1R,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

Guidance literature:: Multi-step reaction with 5 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

4.1: sodium hydroxide; water / ethanol / 2 h / 110 °C / Microwave irradiation

5.1: triethylamine; methanesulfonyl chloride / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; water; tetra-(n-butyl)ammonium iodide; methanesulfonyl chloride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; 3.1: |Mitsunobu Displacement;
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

: 1214271-08-5
(1R,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

Guidance literature:: Multi-step reaction with 4 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

3: sodium hydroxide; water / ethanol / 2 h / 110 °C / Microwave irradiation

4: triethylamine; methanesulfonyl chloride / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

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