(2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one

Base Information

Chemical Name:(2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one
CAS No.:762263-81-0
Molecular Formula:C₄₁H₇₆O₃Si₂
Molecular Weight:673.224
Hs Code.:

(2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one

Synonyms:(2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one

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Chemical Property of (2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one

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Technology Process of (2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one

There total 1 articles about (2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one 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: 66.0%

: 762263-80-9
(1R,5S,6R)-1-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-5-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-6-methylbicyclo[4.1.0]heptan-2-one

: 762263-81-0
(2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one

Guidance literature:: With ammonia; lithium; In tetrahydrofuran; tert-butyl alcohol; at -78 ℃; for 1.5h;
DOI:10.1039/b406820c

Reference yield: 80.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 762263-81-0
(2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one

: 762263-82-1
(2S,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethyl-1-methylenecyclohexane

Guidance literature:: Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.25h;

(2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1039/b406820c

Reference yield:

: 762263-81-0
(2R,4S)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldimethylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethylcyclohexan-1-one

: 762263-83-2
(2S,4S)-2-[(E)-5'-hydroxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-hydroxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3,3-dimethyl-1-methylenecyclohexane

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaHMDS / tetrahydrofuran / 0.25 h / 0 °C

1.2: 80 percent / tetrahydrofuran / 5 h / 20 °C

2.1: 97 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; In tetrahydrofuran; 1.2: Wittig methylenation;
DOI:10.1039/b406820c