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

Base Information

• Chemical Name: 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-one
• CAS No.: 473312-93-5
• Molecular Formula: C₅₀H₇₆O₃Si₂
• Molecular Weight: 781.323

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

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

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

There total 21 articles about 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-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: 93.0%

(1SR,4RS)-2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-ol → 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-one (473312-93-5)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃; for 2h;

DOI:10.1039/b406820c

Reference yield: 91.0%

methylmagnesium bromide (75-16-1) + 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one (762263-74-1) → 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-one (473312-93-5)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1039/b406820c

Reference yield:

methylmagnesium bromide (75-16-1) + 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-3-methoxy-2-cyclohexen-1-one (762263-73-0) + (6Z,10E)-12-bromo-6-tert-butyldiphenylsilyloxymethyl-2,10-dimethyl-2,6,10-dodecatriene (473312-91-3) → 2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-4-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methyl-2-cyclohexen-1-one (473312-93-5)

Guidance literature:

2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-3-methoxy-2-cyclohexen-1-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

(6Z,10E)-12-bromo-6-tert-butyldiphenylsilyloxymethyl-2,10-dimethyl-2,6,10-dodecatriene; at -90 - 20 ℃;

methylmagnesium bromide; In tetrahydrofuran; at 5 - 20 ℃;

DOI:10.1016/S0040-4039(02)01193-0

upstream raw materials:

methylmagnesium bromide

2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-3-methoxy-2-cyclohexen-1-one

(6Z,10E)-12-bromo-6-tert-butyldiphenylsilyloxymethyl-2,10-dimethyl-2,6,10-dodecatriene

2-[(E)-5'-tert-butyldimethylsilyloxy-3'-methyl-3'-pentenyl]-6-[(2''E,6''Z)-7''-tert-butyldiphenylsilyloxymethyl-3'',11''-dimethyl-2'',6'',10''-dodecatrienyl]-3-methoxy-2-cyclohexen-1-one

Downstream raw materials:

(1S,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-methyl-2-cyclohexen-1-ol

(1R,4R)-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-methyl-2-cyclohexen-1-ol

(2S,1'R,4'R)-2-[(E)-5''-hydroxy-3''-methyl-3''-pentenyl]-4-[(2'''E,6'''Z)-7'''-hydroxymethyl-3''',11'''-dimethyl-2''',6''',10'''-dodecatrienyl]-3-methyl-2-cyclohexen-1-yl 2-methoxy-2-(1-naphthyl)propionate

(2S,1'S,4'S)-2-[(E)-5''-hydroxy-3''-methyl-3''-pentenyl]-4-[(2'''E,6'''Z)-7'''-hydroxymethyl-3''',11'''-dimethyl-2''',6''',10'''-dodecatrienyl]-3-methyl-2-cyclohexen-1-yl 2-methoxy-2-(1-naphthyl)propionate

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