(5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate

Base Information

• Chemical Name: (5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate
• CAS No.: 184528-51-6
• Molecular Formula: C₂₇H₃₈O₄Si
• Molecular Weight: 454.682
• Mol file: 184528-51-6.mol

Synonyms:(5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate

Chemical Property of (5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate

There total 2 articles about (5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate 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: 90.0%

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) + (E)-(3R)-Methyl 3-(dimethylphenylsilyl)hex-4-enoate (136174-52-2) → (5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate (184528-51-6)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃;

DOI:10.1021/ja962877x

Reference yield:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) + (E)-(3R)-Methyl 3-(dimethylphenylsilyl)hex-4-enoate (136174-52-2) → (E)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5,7-dimethyl-oct-3-enoic acid methyl ester + (5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate (184528-51-6)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 - -30 ℃; for 49h; Title compound not separated from byproducts.;

DOI:10.1021/jo001767c

Reference yield:

(5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate (184528-51-6) → (2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane (251099-50-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 92 percent / aq. HCl / methanol / 20 °C

2.1: 2,4-lutidine / CH₂Cl₂ / -78 °C

3.1: O₃ / methanol; pyridine

3.2: Me₂S / methanol; pyridine

4.1: 87 percent / TiCl₄ / CH₂Cl₂ / -78 - -30 °C

5.1: HF*pyridine; pyridine / tetrahydrofuran / 1 h / 0 °C

6.1: 2.29 g / imidazole / dimethylformamide / 4 h / 20 °C

7.1: 99 percent / p-toluenesulfonic acid monohydrate / 0.75 h / 20 °C

8.1: O₃; pyridine / methanol / -78 °C

8.2: Me₂S / methanol / 4 h / -78 - 20 °C

9.1: 1.09 g / NaBH₄ / methanol / 0.5 h / 0 °C

10.1: 98 percent / I₂; triphenylphosphine; imidazole / CH₂Cl₂ / 12.25 h / 0 - 20 °C

11.1: t-BuLi / pentane / 0.5 h / -78 - 20 °C

11.2: ZnCl₂ / tetrahydrofuran; pentane / 0.25 h / -78 °C

11.3: 82 percent / Pd(PPh₃)4; LiCl / tetrahydrofuran; pentane / -78 - 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; 2,4-lutidine; iodine; tert.-butyl lithium; titanium tetrachloride; pyridine hydrogenfluoride; ozone; triphenylphosphine; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; pentane;

DOI:10.1021/ja020853m

upstream raw materials:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

(E)-(3R)-Methyl 3-(dimethylphenylsilyl)hex-4-enoate

Downstream raw materials:

(2S,3S,4R,5R,6S)-7-(tert-butyldiphenylsilyloxy)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-heptanol

(2R,3R,4S,5R,6S)-1-iodo-7-(tert-butyldiphenylsilyloxy)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-heptane

methyl-(5S,6S,7R,8R,9S)-(E)-10-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7,9-trimethyl-3-decenoate

methyl-(5S,6S,7R,8R,9S)-(E)-10-(tert-butyldiphenylsilyloxy)-6,8-(isopropylidenedioxy)-5,7,9-trimethyl-3-decenoate