(5Z,7E)-2-bromo-9-(tert-butyldiphenylsilyloxy)-(S)-4-methoxy-8-methylnona-5,7-dien-3-one

Base Information

Chemical Name:(5Z,7E)-2-bromo-9-(tert-butyldiphenylsilyloxy)-(S)-4-methoxy-8-methylnona-5,7-dien-3-one
CAS No.:1402167-36-5
Molecular Formula:C₂₇H₃₅BrO₃Si
Molecular Weight:515.563
Hs Code.:

Synonyms:(5Z,7E)-2-bromo-9-(tert-butyldiphenylsilyloxy)-(S)-4-methoxy-8-methylnona-5,7-dien-3-one

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Chemical Property of (5Z,7E)-2-bromo-9-(tert-butyldiphenylsilyloxy)-(S)-4-methoxy-8-methylnona-5,7-dien-3-one

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Technology Process of (5Z,7E)-2-bromo-9-(tert-butyldiphenylsilyloxy)-(S)-4-methoxy-8-methylnona-5,7-dien-3-one

There total 7 articles about (5Z,7E)-2-bromo-9-(tert-butyldiphenylsilyloxy)-(S)-4-methoxy-8-methylnona-5,7-dien-3-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: 64.0%

: 1402167-35-4
(5Z,7E)-9-(tert-butyldiphenylsilyloxy)-(S)-4-methoxy-8-methylnona-5,7-dien-3-one

: 1402167-36-5
(5Z,7E)-2-bromo-9-(tert-butyldiphenylsilyloxy)-(S)-4-methoxy-8-methylnona-5,7-dien-3-one

Guidance literature:: With phenyltrimethylammonium tribromide; In tetrahydrofuran; at 0 ℃; for 16.1667h;
DOI:10.1002/chem.201201600

Reference yield:

: 1402167-32-1
(2E,4Z)-7-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-(S)-6-methoxy-2-methylhepta-2,4-diene

: 1402167-36-5
(5Z,7E)-2-bromo-9-(tert-butyldiphenylsilyloxy)-(S)-4-methoxy-8-methylnona-5,7-dien-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: camphor-10-sulfonic acid / methanol; dichloromethane / 2 h / 0 °C

2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / 85 °C

3: tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C

4: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

5: phenyltrimethylammonium tribromide / tetrahydrofuran / 16.17 h / 0 °C

With camphor-10-sulfonic acid; phenyltrimethylammonium tribromide; Dess-Martin periodane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1002/chem.201201600

Reference yield:

: 1402167-33-2
(3Z,5E)-7-(tert-butyldiphenylsilyloxy)-(S)-2-methoxy-6-methylhepta-3,5-dien-1-ol

: 1402167-36-5
(5Z,7E)-2-bromo-9-(tert-butyldiphenylsilyloxy)-(S)-4-methoxy-8-methylnona-5,7-dien-3-one

Guidance literature:: Multi-step reaction with 4 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / 85 °C

2: tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C

3: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

4: phenyltrimethylammonium tribromide / tetrahydrofuran / 16.17 h / 0 °C

With phenyltrimethylammonium tribromide; Dess-Martin periodane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1002/chem.201201600