3-Octenoic acid, 6-hydroxy-5,7-dimethyl-8-(phenylmethoxy)-, methyl ester, (3E,5S,6R,7S)-

Base Information

• Chemical Name: 3-Octenoic acid, 6-hydroxy-5,7-dimethyl-8-(phenylmethoxy)-, methyl ester, (3E,5S,6R,7S)-
• CAS No.: 184528-50-5
• Molecular Formula: C18H26O4
• Molecular Weight: 306.402
• Mol file: 184528-50-5.mol

Synonyms:

Chemical Property of 3-Octenoic acid, 6-hydroxy-5,7-dimethyl-8-(phenylmethoxy)-, methyl ester, (3E,5S,6R,7S)-

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Octenoic acid, 6-hydroxy-5,7-dimethyl-8-(phenylmethoxy)-, methyl ester, (3E,5S,6R,7S)-

There total 1 articles about 3-Octenoic acid, 6-hydroxy-5,7-dimethyl-8-(phenylmethoxy)-, methyl ester, (3E,5S,6R,7S)- 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: 85.0%

(2S)-3-(benzyloxy)-2-methylpropanal (79027-28-4) + methyl (3S,4E)-3-(dimethylphenylsilyl)-4-hexenoate (136314-66-4) → (E)-(5S,6R,7S)-8-Benzyloxy-6-hydroxy-5,7-dimethyl-oct-3-enoic acid methyl ester (184528-50-5)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 - -20 ℃;

DOI:10.1021/ja043168j

Reference yield: 97.0%

t-butyldimethylsiyl triflate (69739-34-0) + (E)-(5S,6R,7S)-8-Benzyloxy-6-hydroxy-5,7-dimethyl-oct-3-enoic acid methyl ester (184528-50-5) → (3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester (444109-26-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ja043168j

Reference yield:

(E)-(5S,6R,7S)-8-Benzyloxy-6-hydroxy-5,7-dimethyl-oct-3-enoic acid methyl ester (184528-50-5) → (R)-2-[(2S,4S,5S,6S)-6-((3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13S,14S,15S)-14-Carbamoyloxy-12-hydroxy-2,6-bis-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester (851889-87-7)

Guidance literature:

Multi-step reaction with 26 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

2.1: ozone / methanol / -78 °C

2.2: dimethyl sulfide / methanol / -78 - 0 °C

3.1: 10.7 g / triphenylphosphine; 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -20 °C

4.2: 79 percent / tetrahydrofuran; hexane / 8 h / -78 - 0 °C

5.1: Cp₂Zr(H)Cl / tetrahydrofuran / 1.08 h / 20 - 55 °C

5.2: 92 percent / I₂ / tetrahydrofuran / 0.33 h / 20 °C

6.1: ZnCl₂ / tetrahydrofuran; diethyl ether / 0.25 h / 20 °C

6.2: 88 percent / Pd(PPh₃)4 / tetrahydrofuran; diethyl ether / 2 h / 20 °C

7.1: 95 percent / lithium di-tert-butylbiphenyl radical anion / tetrahydrofuran / 2.5 h / -78 °C

8.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

9.1: 5.62 g / triphenylphosphine; 2,6-ludidine / CH₂Cl₂ / 4 h / 0 °C

10.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -20 °C

10.2: 78 percent / tetrahydrofuran; hexane / 10 h / -78 - -30 °C

11.1: diisopropylethyl amine / CH₂Cl₂ / 0.08 h / -78 °C

11.2: Bu₂BOTf / CH₂Cl₂ / 0.75 h / -78 °C

11.3: 76 percent / CH₂Cl₂ / 1 h / -78 °C

12.1: 95 percent / SmI₂ / tetrahydrofuran / 4 h / -10 °C

13.1: KOH / methanol / 20 °C

13.2: 20 percent / silica gel / methanol; hexane

14.1: PPTS / CH₂Cl₂

15.1: 0.47 g / RuCl₂(PPh₃)3 / benzene / 8 h / 20 °C

16.1: NaClO₂; NaH₂PO₄*H₂₀; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

17.1: 0.44 g / benzene; methanol; hexane / 0.25 h

18.1: 83 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 8 h / 0 - 20 °C

19.1: H₂; quinoline / Pd/CaCO₃/Pb / hexane / 8 h / 760 Torr

20.1: 0.397 g / N-iodosuccinimide / acetonitrile; various solvent(s) / 3 h

21.1: TBAF; AcOH / tetrahydrofuran / 36 h / 20 °C

22.1: 0.054 g / diisopropylethylamine; DMAP / CH₂Cl₂ / 8 h / 0 - 20 °C

23.1: 50.0 mg / PdCl₂(dppf); TlOEt / dimethylformamide; tetrahydrofuran / 14 h / 20 °C

24.1: 77 percent / p-TsOH*H₂O / methanol / 1 h / 0 °C

25.1: CH₂Cl₂ / 0.17 h / 20 °C

25.2: 95 percent / K₂CO₃ / methanol / 1.25 h

26.1: 90 percent / NaHCO₃; DDQ; water / CH₂Cl₂ / 2 h

With 2,6-dimethylpyridine; quinoline; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; Schwartz's reagent; tris(triphenylphosphine)ruthenium(II) chloride; n-butyllithium; samarium diiodide; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; water; hydrogen; thallium (I) ethoxide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; lithium 4,4′-di-tert-butylbiphenylide; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 3.1: Corey-Fuchs olefination / 8.1: Swern oxidation / 9.1: Corey-Fuchs olefination / 12.1: Evans-Tischenko reduction / 19.1: Lindlar reduction / 20.1: Kishi iododesilylation / 23.1: Suzuki cross-coupling;

DOI:10.1021/ja043168j

upstream raw materials:

(2S)-3-(benzyloxy)-2-methylpropanal

methyl (3S,4E)-3-(dimethylphenylsilyl)-4-hexenoate

Downstream raw materials:

(3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester

(R)-2-[(2S,4S,5S,6S)-6-((3Z,8Z)-(2S,5S,6S,7S)-6-Hydroxy-9-iodo-2-methoxymethoxy-5,7-dimethyl-deca-3,8-dienyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionic acid methyl ester

(2R,3S,4S,5S,7S,8Z,10S,11S,12S,13Z)-14-iodo-3,5-[(S)-4-methoxybenzilidenedioxy]-7,11-bis-methoxymethoxy-2,4,10,12-tetramethylpentadeca-8,13-dienoic acid methyl ester

(R)-2-[(2S,4S,5S,6S)-6-[(Z)-(2S,5S,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,7-dimethyl-9-trimethylsilanyl-dec-8-en-3-ynyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde