(1R,3R,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl methanesulfonate

Base Information

Chemical Name:(1R,3R,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl methanesulfonate
CAS No.:1609017-82-4
Molecular Formula:C₃₁H₃₇NO₆S
Molecular Weight:551.704
Hs Code.:

Synonyms:(1R,3R,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl methanesulfonate

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

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

There total 10 articles about (1R,3R,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl methanesulfonate 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: 87.0%

: 1214271-07-4
(1R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol

: 124-63-0
methanesulfonyl chloride

: 1609017-82-4
(1R,3R,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl methanesulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 24h; Inert atmosphere;
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

: 1609017-82-4
(1R,3R,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl methanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

4: triethylamine; dmap / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

With dmap; water; methanesulfonyl chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In ethanol; dichloromethane; water;
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

: 1609017-82-4
(1R,3R,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-yl methanesulfonate

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: 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; dmap / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

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