(1R,4aS,4bS,7S,8S,8aS,10aS)-allyl 7-(benzyloxy)-10a-cyano-3-hydroxy-1,4b,8-trimethyl-10-oxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-4-carboxylate

Base Information

Chemical Name:(1R,4aS,4bS,7S,8S,8aS,10aS)-allyl 7-(benzyloxy)-10a-cyano-3-hydroxy-1,4b,8-trimethyl-10-oxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-4-carboxylate
CAS No.:1207384-26-6
Molecular Formula:C₂₉H₃₅NO₅
Molecular Weight:477.601
Hs Code.:

(1R,4aS,4bS,7S,8S,8aS,10aS)-allyl 7-(benzyloxy)-10a-cyano-3-hydroxy-1,4b,8-trimethyl-10-oxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-4-carboxylate

Synonyms:(1R,4aS,4bS,7S,8S,8aS,10aS)-allyl 7-(benzyloxy)-10a-cyano-3-hydroxy-1,4b,8-trimethyl-10-oxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-4-carboxylate

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Chemical Property of (1R,4aS,4bS,7S,8S,8aS,10aS)-allyl 7-(benzyloxy)-10a-cyano-3-hydroxy-1,4b,8-trimethyl-10-oxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-4-carboxylate

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Technology Process of (1R,4aS,4bS,7S,8S,8aS,10aS)-allyl 7-(benzyloxy)-10a-cyano-3-hydroxy-1,4b,8-trimethyl-10-oxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-4-carboxylate

There total 13 articles about (1R,4aS,4bS,7S,8S,8aS,10aS)-allyl 7-(benzyloxy)-10a-cyano-3-hydroxy-1,4b,8-trimethyl-10-oxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-4-carboxylate 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: 82.0%

: 1207384-19-7
(E)-allyl 3-oxohex-4-enoate

: 1207384-25-5
(4aS,5S,6S,8aS)-6-(benzyloxy)-5,8a-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonitrile

: 1207384-26-6
(1R,4aS,4bS,7S,8S,8aS,10aS)-allyl 7-(benzyloxy)-10a-cyano-3-hydroxy-1,4b,8-trimethyl-10-oxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-4-carboxylate

Guidance literature:: With caesium carbonate; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/ol902711b

Reference yield:

: 591-87-7
Allyl acetate

: 1207384-26-6
(1R,4aS,4bS,7S,8S,8aS,10aS)-allyl 7-(benzyloxy)-10a-cyano-3-hydroxy-1,4b,8-trimethyl-10-oxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: caesium carbonate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With caesium carbonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 2.1: |Dess-Martin Oxidation;
DOI:10.1021/jo501122k

Reference yield:

: C₂₀H₂₅NO₂

: 1207384-26-6
(1R,4aS,4bS,7S,8S,8aS,10aS)-allyl 7-(benzyloxy)-10a-cyano-3-hydroxy-1,4b,8-trimethyl-10-oxo-1,2,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.25 h / Inert atmosphere; Reflux

2: caesium carbonate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With caesium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; benzene;
DOI:10.1021/jo501122k