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

Base Information

Chemical Name:(1S,3R,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol
CAS No.:1609017-80-2
Molecular Formula:C₃₀H₃₅NO₄
Molecular Weight:473.612
Hs Code.:

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

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

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

There total 11 articles about (1S,3R,5R,6R,7R,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: 58.0%

: 1609017-77-7
(3R,5R,6R,7R,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-one

: 1609017-80-2
(1S,3R,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 - 22 ℃; for 3h;
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

: 1609017-80-2
(1S,3R,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 4 h / 26 °C

2.1: sodium hydroxide; water / ethanol / 1 h / 110 °C / Microwave irradiation

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

4.1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

4.2: 3 h / -78 - 22 °C

5.1: L-Selectride / tetrahydrofuran / 3 h / -78 - 22 °C

With oxalyl dichloride; water; L-Selectride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; 4.1: |Swern Oxidation;
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

: 1609017-80-2
(1S,3R,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

Guidance literature:: Multi-step reaction with 6 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: sodium hydroxide; water / ethanol / 1 h / 110 °C / Microwave irradiation

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

5.1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

5.2: 3 h / -78 - 22 °C

6.1: L-Selectride / tetrahydrofuran / 3 h / -78 - 22 °C

With oxalyl dichloride; water; tetra-(n-butyl)ammonium iodide; L-Selectride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; 5.1: |Swern Oxidation;
DOI:10.1021/jo5005923