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

Base Information

• Chemical Name: [3R,4S,5S,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-11-[(methoxymethyl)oxy]-2,4,8,10-tetramethyltetradec-13-en-5-ol-7-one
• CAS No.: 143292-45-9
• Molecular Formula: C₃₅H₆₂O₈Si
• Molecular Weight: 638.958
• Mol file: 143292-45-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 20 articles about [3R,4S,5S,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-11-[(methoxymethyl)oxy]-2,4,8,10-tetramethyltetradec-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: 50.0%

(2R,3R)-2,4-dimethyl-3-<(4-methoxybenzyloxy)oxy>pentanal (143245-40-3) + [3S,4R,5R,6R,7S]-4-[(tert-butyldimethylsilyl)oxy]-3,5-dimethyl-7-methoxy-6-[(methoxymethyl)oxy]non-8-en-2-one (143245-41-4) → [3R,4S,5S,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-11-[(methoxymethyl)oxy]-2,4,8,10-tetramethyltetradec-13-en-5-ol-7-one (143292-45-9) + [3R,4S,5R,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-11-[(methoxymethyl)oxy]-2,4,8,10-tetramethyltetradec-13-en-5-ol-7-one (143245-39-0)

Guidance literature:

[3S,4R,5R,6R,7S]-4-[(tert-butyldimethylsilyl)oxy]-3,5-dimethyl-7-methoxy-6-[(methoxymethyl)oxy]non-8-en-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.333333h;

(2R,3R)-2,4-dimethyl-3-<(4-methoxybenzyloxy)oxy>pentanal; In tetrahydrofuran; at -78 ℃; for 0.00833333h;

DOI:10.1021/jo016413f

Reference yield:

[2R,3R,4S,5R,6R,7S]-4-[(tert-butyldimethylsilyl)oxy]-3,5-dimethyl-7-methoxy-6-[(methoxymethyl)oxy]non-8-en-2-ol (443283-33-8) → [3R,4S,5S,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-11-[(methoxymethyl)oxy]-2,4,8,10-tetramethyltetradec-13-en-5-ol-7-one (143292-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: celite; molecular sieves 4 Angstroem; sodium acetate / pyridinium chlorochromate / CH₂Cl₂ / 3 h / 23 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.33 h / -78 °C

2.2: 6 percent / tetrahydrofuran / 0.01 h / -78 °C

With 4 A molecular sieve; Celite; sodium acetate; lithium hexamethyldisilazane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo016413f

Reference yield:

ethyl anti-(2R,3R)-2-methyl-3-hydroxybutanoate (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) → [3R,4S,5S,8S,9R,10R,11R,12S]-9-[(tert-butyldimethylsilyl)oxy]-12-methoxy-3-[(4-methoxybenzyl)oxy]-11-[(methoxymethyl)oxy]-2,4,8,10-tetramethyltetradec-13-en-5-ol-7-one (143292-45-9)

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: 97 percent / N,N-diisopropylethyl amine / 96 h

11.1: dichlorodicyanoquinone; water / CH₂Cl₂ / 0.5 h / 0 °C

12.1: celite; molecular sieves 4 Angstroem; sodium acetate / pyridinium chlorochromate / CH₂Cl₂ / 3 h / 23 °C

13.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.33 h / -78 °C

13.2: 6 percent / tetrahydrofuran / 0.01 h / -78 °C

With 2,6-dimethylpyridine; chromium dichloride; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; trimethylsilyl iodide; 4 A molecular sieve; Celite; water; sodium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; 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

upstream raw materials:

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

[3S,4R,5R,6R,7S]-4-[(tert-butyldimethylsilyl)oxy]-3,5-dimethyl-7-methoxy-6-[(methoxymethyl)oxy]non-8-en-2-one

ethyl anti-(2R,3R)-2-methyl-3-hydroxybutanoate

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