[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(triethylsilyl)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-[(triethylsilyl)oxy]tetradec-13-en-5-ol-7-one
CAS No.:155250-79-6
Molecular Formula:C₃₉H₇₂O₇Si₂
Molecular Weight:709.167
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-[(triethylsilyl)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-[(triethylsilyl)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-[(triethylsilyl)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-[(triethylsilyl)oxy]tetradec-13-en-5-ol-7-one

There total 18 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-[(triethylsilyl)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: 74.0%

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

: 143245-48-1
[3S,4R,5R,6R,7S]-4-[(tert-butyldimethylsilyl)oxy]-3,5-dimethyl-7-methoxy-6-[(triethylsilyl)oxy]non-8-en-2-one

: 441354-76-3
[3R,4S,5S,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(triethylsilyl)oxy]tetradec-13-en-5-ol-7-one

: 155250-79-6
[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(triethylsilyl)oxy]tetradec-13-en-5-ol-7-one

Guidance literature:: [3S,4R,5R,6R,7S]-4-[(tert-butyldimethylsilyl)oxy]-3,5-dimethyl-7-methoxy-6-[(triethylsilyl)oxy]non-8-en-2-one; With thallium chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1h;

(2R,3R)-2,4-dimethyl-3-<(4-methoxybenzyloxy)oxy>pentanal; In dichloromethane; for 0.416667h;
DOI:10.1021/jo016413f

Reference yield:

: 27372-03-8,51898-35-2,51898-36-3,63647-69-8,78088-27-4,78088-28-5,86853-34-1,92282-67-2,86853-33-0
ethyl anti-(2R,3R)-2-methyl-3-hydroxybutanoate

: 155250-79-6
[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(triethylsilyl)oxy]tetradec-13-en-5-ol-7-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: 94 percent / lithium aluminum hydride / diethyl ether / 1 h

2.1: 84 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

3.1: 98 percent / DIBAL-H / CH₂Cl₂ / 2.5 h / 0 °C

4.1: 9.8 g / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

5.1: 9.98 g / toluene / -78 °C

6.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -40 °C

7.1: 98 percent / N-methylmorpholine N-oxide / osmium tetroxide / acetone; tetrahydrofuran / 8 h / pH 7

8.1: 94 percent / NaIO₄ / tetrahydrofuran / 1.5 h / 23 °C / pH 7

9.1: 76 percent / chromium(II) chloride; iodotrimethylsilane / tetrahydrofuran / 7 h / -45 °C

10.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -50 °C

11.1: 95 percent / dihydrodicyanoquinone; water / CH₂Cl₂ / 0.33 h / 0 °C

12.1: 72 percent / molecular sieves 4 Angstroem; sodium acetate; celite / pyridinium chlorochromate / CH₂Cl₂ / 23 °C

13.1: TiCl; diisopropylethylamine / CH₂Cl₂ / 1 h / -78 °C

13.2: 74 percent / CH₂Cl₂ / 0.42 h

With 2,6-dimethylpyridine; chromium dichloride; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; thallium chloride; trimethylsilyl iodide; 4 A molecular sieve; Celite; dihydrodicyanoquinone; water; sodium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; osmium(VIII) oxide; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; benzene; 4.1: Swern oxidation / 9.1: Takai reaction;
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

: 155250-79-6
[3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-2,4,8,10-tetramethyl-11-[(triethylsilyl)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: TiCl; diisopropylethylamine / CH₂Cl₂ / 1 h / -78 °C

7.2: 74 percent / CH₂Cl₂ / 0.42 h

With pyridine; sodium periodate; lithium aluminium tetrahydride; thallium chloride; tributyl borane; 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