(3aS,4R,5S,6S,8R,9R,9aR,10R)-2-(Quinuclidin-4-ylsulfanyl)acetic acid 5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester

Base Information

Chemical Name:(3aS,4R,5S,6S,8R,9R,9aR,10R)-2-(Quinuclidin-4-ylsulfanyl)acetic acid 5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester
CAS No.:224296-26-8
Molecular Formula:C₂₉H₄₅NO₄S
Molecular Weight:503.747
Hs Code.:

(3aS,4R,5S,6S,8R,9R,9aR,10R)-2-(Quinuclidin-4-ylsulfanyl)acetic acid 5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester

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Chemical Property of (3aS,4R,5S,6S,8R,9R,9aR,10R)-2-(Quinuclidin-4-ylsulfanyl)acetic acid 5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester

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Technology Process of (3aS,4R,5S,6S,8R,9R,9aR,10R)-2-(Quinuclidin-4-ylsulfanyl)acetic acid 5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester

There total 7 articles about (3aS,4R,5S,6S,8R,9R,9aR,10R)-2-(Quinuclidin-4-ylsulfanyl)acetic acid 5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester 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%

: 60924-38-1
{(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldeca hydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacyclo-octen-8-yl methanesulfonyloxyacetate}

: 224296-93-9
1-azoniabicyclo[2.2.2]octane-4-thiol chloride

: 224296-26-8
(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl-[1-azoniabicyclo[2.2.2]octane-4-thio]acetate

Guidance literature:: 1-azoniabicyclo[2.2.2]octane-4-thiol chloride; With sodium hydroxide; In methanol; at 13 - 20 ℃; for 1h; Inert atmosphere; Large scale;

{(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldeca hydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacyclo-octen-8-yl methanesulfonyloxyacetate}; In methanol; at 20 ℃; for 1.5h; Inert atmosphere; Large scale;
DOI:10.1021/op300263w

Reference yield:

: 40110-55-2
ethyl 2-(1-benzylpiperidine-4-ylidene)acetate

: 224296-26-8
(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl-[1-azoniabicyclo[2.2.2]octane-4-thio]acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydroxide / N,N-dimethyl-formamide; toluene / 0.5 h / Inert atmosphere

1.2: 13.5 h / 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / dichloromethane / 1.5 h / Inert atmosphere; Reflux; Large scale

4.1: ammonia; sodium / isopropyl alcohol / 2.5 h / -33 °C / Inert atmosphere; Cooling with ice; Large scale

4.2: 0.33 h / Inert atmosphere; Large scale

5.1: sodium hydroxide / methanol / 1 h / 13 - 20 °C / Inert atmosphere; Large scale

5.2: 1.5 h / 20 °C / Inert atmosphere; Large scale

With lithium aluminium tetrahydride; ammonia; sodium; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1021/op300263w

Reference yield:

: 1408290-28-7
ethyl 2-[1-benzyl-4-(benzylsulfanyl)piperidin-4-yl]acetate

: 224296-26-8
(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl-[1-azoniabicyclo[2.2.2]octane-4-thio]acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / dichloromethane / 1.5 h / Inert atmosphere; Reflux; Large scale

3.1: ammonia; sodium / isopropyl alcohol / 2.5 h / -33 °C / Inert atmosphere; Cooling with ice; Large scale

3.2: 0.33 h / Inert atmosphere; Large scale

4.1: sodium hydroxide / methanol / 1 h / 13 - 20 °C / Inert atmosphere; Large scale

4.2: 1.5 h / 20 °C / Inert atmosphere; Large scale

With lithium aluminium tetrahydride; ammonia; sodium; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol;
DOI:10.1021/op300263w