(4S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)-2-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbonyl)pentanenitrile

Base Information

Chemical Name:(4S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)-2-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbonyl)pentanenitrile
CAS No.:1344118-83-7
Molecular Formula:C₃₇H₅₆INO₃Si₂
Molecular Weight:745.932
Hs Code.:

(4S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)-2-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbonyl)pentanenitrile

Synonyms:(4S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)-2-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbonyl)pentanenitrile

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Chemical Property of (4S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)-2-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbonyl)pentanenitrile

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Technology Process of (4S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)-2-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbonyl)pentanenitrile

There total 16 articles about (4S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)-2-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbonyl)pentanenitrile 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:

: C₃₇H₅₈INO₃Si₂

: 1344118-83-7
(4S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)-2-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbonyl)pentanenitrile

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; Inert atmosphere;
DOI:10.1021/ol202748e

Reference yield:

: 1344118-62-2
(S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)pentanenitrile

: 1344118-79-1
(1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbaldehyde

: 1344118-83-7
(4S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)-2-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbonyl)pentanenitrile

Guidance literature:: (S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)pentanenitrile; With n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

(1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;
DOI:10.1021/ol202748e

Reference yield:

: 1192233-13-8
(+)-(1S,2S,4aS,4bS,6R,8aR,9S,9aS)-9-hydroxy-6-methyl-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carboxylic acid methyl ester

: 1344118-83-7
(4S)-4-((tert-butyldimethylsilyl)oxy)-5-(4-iodophenyl)-2-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-6-methyl-9-((trimethylsilyl)oxy)-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluorene-1-carbonyl)pentanenitrile

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C / Inert atmosphere

3.1: 1H-imidazole / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

4.2: 0.25 h / -78 °C / Inert atmosphere

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 4.2: Aldol condensation;
DOI:10.1021/ol202748e