[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]tetradec-13-en-5-ol-7-one

Base Information

Chemical Name:[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]tetradec-13-en-5-ol-7-one
CAS No.:155250-80-9
Molecular Formula:C₄₀H₆₂O₈Si
Molecular Weight:699.013
Hs Code.:

[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]tetradec-13-en-5-ol-7-one

Synonyms:[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]tetradec-13-en-5-ol-7-one

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Chemical Property of [3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]tetradec-13-en-5-ol-7-one

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Technology Process of [3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]tetradec-13-en-5-ol-7-one

There total 6 articles about [3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]tetradec-13-en-5-ol-7-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: 63.0%

: 143245-40-3
(2R,3R)-2,4-dimethyl-3-<(4-methoxybenzyloxy)oxy>pentanal

: Benzoic acid (1R,2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-methoxy-allyl)-2,4-dimethyl-5-oxo-hexyl ester

: [3R,4S,5S,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]-tetradec-13-en-5-ol-7-one

: 155250-80-9
[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]tetradec-13-en-5-ol-7-one

Guidance literature:: Benzoic acid (1R,2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-methoxy-allyl)-2,4-dimethyl-5-oxo-hexyl ester; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1h;

(2R,3R)-2,4-dimethyl-3-<(4-methoxybenzyloxy)oxy>pentanal; In tetrahydrofuran; at -78 ℃; for 0.416667h; Further stages.;
DOI:10.1021/jo016413f

Reference yield:

: 108735-30-4
[3R,4S,4'S]-4-[acyl(4'-isopropyl-2'-oxazolidone)]-2-methylhex-5-en-3-ol

: 155250-80-9
[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]tetradec-13-en-5-ol-7-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: tributylborane; acetic acid / tetrahydrofuran / 1.5 h / 23 °C

1.2: lithium borohydride / tetrahydrofuran / 1 h / 0 °C

1.3: 85 percent / H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C / pH 7

2.1: 81 percent / pyridine / 4 h / 23 °C

3.1: 66 percent / lithium aluminum hydride / diethyl ether / -25 °C

4.1: sodium hydride / dimethylsulfoxide; tetrahydrofuran / 0.5 h / 23 °C

4.2: 86 percent / tetrahydrofuran; dimethylsulfoxide / 23 °C

5.1: N-methylmorpholine N-oxide / osmium tetroxide / acetone; tetrahydrofuran; H₂O / 3 h / 23 °C / pH 7.0

6.1: aq. NaIO₄ / tetrahydrofuran; H₂O / 23 °C / pH 7.0

7.1: TiCl₄; diisopropylethylamine / CH₂Cl₂ / 1 h / -78 °C

7.2: 63 percent / tetrahydrofuran / 0.42 h / -78 °C

With pyridine; sodium periodate; lithium aluminium tetrahydride; tributyl borane; titanium tetrachloride; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetone;
DOI:10.1021/jo016413f

Reference yield:

: 443283-04-3
[3R,4R]-3-hydroxymethyl-5-methylhex-1-en-4-ol

: 155250-80-9
[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(benzoyl)oxy]tetradec-13-en-5-ol-7-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 81 percent / pyridine / 4 h / 23 °C

2.1: 66 percent / lithium aluminum hydride / diethyl ether / -25 °C

3.1: sodium hydride / dimethylsulfoxide; tetrahydrofuran / 0.5 h / 23 °C

3.2: 86 percent / tetrahydrofuran; dimethylsulfoxide / 23 °C

4.1: N-methylmorpholine N-oxide / osmium tetroxide / acetone; tetrahydrofuran; H₂O / 3 h / 23 °C / pH 7.0

5.1: aq. NaIO₄ / tetrahydrofuran; H₂O / 23 °C / pH 7.0

6.1: TiCl₄; diisopropylethylamine / CH₂Cl₂ / 1 h / -78 °C

6.2: 63 percent / tetrahydrofuran / 0.42 h / -78 °C

With pyridine; sodium periodate; lithium aluminium tetrahydride; titanium tetrachloride; sodium hydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetone;
DOI:10.1021/jo016413f