(3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester

Base Information

Chemical Name:(3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester
CAS No.:851889-68-4
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

Synonyms:(3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester

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Chemical Property of (3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester

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Technology Process of (3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester

There total 1 articles about (3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester 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:

: 147623-96-9
(3S,4E)-Methyl 4-methyl-3-(dinethylphenylsilyl)hexenoate

: 851889-68-4
(3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 5.0 g / HCl / methanol / 2 h

2: 90 percent / p-toluenesulfonic acid / dimethylformamide / 3 h / 20 °C

With hydrogenchloride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja043168j

Reference yield: 95.0%

: 851889-68-4
(3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester

: 652986-45-3
(3R,4R,5S)-4,6-[(R)-4-methoxy-benzylidenedioxy]-3,5-dimethyl-2-butanone

Guidance literature:: (3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester; With pyridine; ozone; In methanol; at -78 ℃;

With dimethylsulfide; In methanol; at -78 - 0 ℃;
DOI:10.1021/ja043168j

Reference yield:

: 851889-68-4
(3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester

: 851889-87-7
(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

Guidance literature:: Multi-step reaction with 17 steps

1.1: ozone; pyridine / methanol / -78 °C

1.2: 95 percent / dimethyl sulfide / methanol / -78 - 0 °C

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

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

2.3: 76 percent / CH₂Cl₂ / 1 h / -78 °C

3.1: 95 percent / SmI₂ / tetrahydrofuran / 4 h / -10 °C

4.1: KOH / methanol / 20 °C

4.2: 20 percent / silica gel / methanol; hexane

5.1: PPTS / CH₂Cl₂

6.1: 0.47 g / RuCl₂(PPh₃)3 / benzene / 8 h / 20 °C

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

8.1: 0.44 g / benzene; methanol; hexane / 0.25 h

9.1: 83 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 8 h / 0 - 20 °C

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

11.1: 0.397 g / N-iodosuccinimide / acetonitrile; various solvent(s) / 3 h

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

13.1: 0.054 g / diisopropylethylamine; DMAP / CH₂Cl₂ / 8 h / 0 - 20 °C

14.1: 50.0 mg / PdCl₂(dppf); TlOEt / dimethylformamide; tetrahydrofuran / 14 h / 20 °C

15.1: 77 percent / p-TsOH*H₂O / methanol / 1 h / 0 °C

16.1: CH₂Cl₂ / 0.17 h / 20 °C

16.2: 95 percent / K₂CO₃ / methanol / 1.25 h

17.1: 90 percent / NaHCO₃; DDQ; water / CH₂Cl₂ / 2 h

With pyridine; quinoline; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; tris(triphenylphosphine)ruthenium(II) chloride; samarium diiodide; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; water; hydrogen; thallium (I) ethoxide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 3.1: Evans-Tischenko reduction / 10.1: Lindlar reduction / 11.1: Kishi iododesilylation / 14.1: Suzuki cross-coupling;
DOI:10.1021/ja043168j