(E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid

Base Information

• Chemical Name: (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid
• CAS No.: 929118-02-5
• Molecular Formula: C₂₄H₃₈O₁₀
• Molecular Weight: 486.56
• Mol file: 929118-02-5.mol

Synonyms:(E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid

Chemical Property of (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid

There total 19 articles about (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid 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:

(1E)-5-[(tert-butyldiphenylsilyl)oxy]-1-trimethylsilyl-1-penten-3-ol (851278-45-0) → (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid (929118-02-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 43 percent / t-BuOOH; D-(-)-DIPT; Ti(O-i-Pr)4 / CH₂Cl₂ / 13 h / -20 °C

2.1: Br₂ / CH₂Cl₂ / 0.25 h / cooling

3.1: 1.47 g / Bu₄NF / tetrahydrofuran / 0.25 h / cooling

4.1: MeLi / NiCl₂(dppf) / diethyl ether; tetrahydrofuran / 0.25 h / 0 °C

4.2: 76 percent / diethyl ether; tetrahydrofuran / 20 °C

5.1: 70 percent / NaHCO₃; m-CPBA / CH₂Cl₂ / 0.83 h / 0 °C

6.1: 68 percent / Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 8 - 11 °C

7.1: 82 percent / MeLi / tetrahydrofuran; diethyl ether / 2 h / 20 °C

8.1: 99 percent / ethyldiisopropylamine / CH₂Cl₂ / 40 °C

9.1: 100 percent / Bu₄NF / tetrahydrofuran / 2 h / 40 °C

10.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -45 - 0 °C

11.1: NaClO₂ / 2-methyl-propan-2-ol; aq. phosphate buffer; various solvent(s) / 2 h / 20 °C / pH 3.6

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium chlorite; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; bromine; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium iodide; In tetrahydrofuran; phosphate buffer; diethyl ether; dichloromethane; tert-butyl alcohol; 1.1: Sharpless epoxidation / 10.1: Swern oxidation;

DOI:10.1021/jo0623890

Reference yield:

(S)-1-chloro-2-hydroxy-5-trimethylsilyl-4-pentyne (148516-13-6) → (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid (929118-02-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 85 percent / LiAlH₄ / tetrahydrofuran / 4 h / 20 °C

2.1: NaH; NaI / tetrahydrofuran; H₂O; various solvent(s) / 0.5 h / 55 °C

3.1: tetrahydrofuran / 2.5 h / -35 - 20 °C

4.1: tetrahydrofuran / Heating

5.1: 422 mg / tetrahydrofuran / 48 h / 20 °C

6.1: MeLi / NiCl₂(dppf) / diethyl ether; tetrahydrofuran / 0.25 h / 0 °C

6.2: 76 percent / diethyl ether; tetrahydrofuran / 20 °C

7.1: 70 percent / NaHCO₃; m-CPBA / CH₂Cl₂ / 0.83 h / 0 °C

8.1: 68 percent / Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 8 - 11 °C

9.1: 82 percent / MeLi / tetrahydrofuran; diethyl ether / 2 h / 20 °C

10.1: 99 percent / ethyldiisopropylamine / CH₂Cl₂ / 40 °C

11.1: 100 percent / Bu₄NF / tetrahydrofuran / 2 h / 40 °C

12.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -45 - 0 °C

13.1: NaClO₂ / 2-methyl-propan-2-ol; aq. phosphate buffer; various solvent(s) / 2 h / 20 °C / pH 3.6

With sodium chlorite; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium iodide; In tetrahydrofuran; phosphate buffer; diethyl ether; dichloromethane; water; tert-butyl alcohol; 12.1: Swern oxidation;

DOI:10.1021/jo0623890

Reference yield:

(R)-5-(trimethylsilyl)pent-4-yn-2-ol (460348-12-3) → (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid (929118-02-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NaH; NaI / tetrahydrofuran; H₂O; various solvent(s) / 0.5 h / 55 °C

2.1: tetrahydrofuran / 2.5 h / -35 - 20 °C

3.1: tetrahydrofuran / Heating

4.1: 422 mg / tetrahydrofuran / 48 h / 20 °C

5.1: MeLi / NiCl₂(dppf) / diethyl ether; tetrahydrofuran / 0.25 h / 0 °C

5.2: 76 percent / diethyl ether; tetrahydrofuran / 20 °C

6.1: 70 percent / NaHCO₃; m-CPBA / CH₂Cl₂ / 0.83 h / 0 °C

7.1: 68 percent / Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 8 - 11 °C

8.1: 82 percent / MeLi / tetrahydrofuran; diethyl ether / 2 h / 20 °C

9.1: 99 percent / ethyldiisopropylamine / CH₂Cl₂ / 40 °C

10.1: 100 percent / Bu₄NF / tetrahydrofuran / 2 h / 40 °C

11.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -45 - 0 °C

12.1: NaClO₂ / 2-methyl-propan-2-ol; aq. phosphate buffer; various solvent(s) / 2 h / 20 °C / pH 3.6

With sodium chlorite; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium iodide; In tetrahydrofuran; phosphate buffer; diethyl ether; dichloromethane; water; tert-butyl alcohol; 11.1: Swern oxidation;

DOI:10.1021/jo0623890

upstream raw materials:

(R)-1-methoxy-4-((pent-4-yn-2-yloxy)methyl)benzene

(1'E,4'R)-2-[4'-(4-methoxybenzyloxy)-1'-pentenyl]-5,5-dimethyl-1,3,2-dioxaborinane

(1Z,3S)-1-bromo-5-[(tert-butyldiphenylsilyl)oxy]-1-penten-3-ol

(1E,3S)-5-[(tert-butyldiphenylsilyl)oxy]-1-trimethylsilyl-1-penten-3-ol

Downstream raw materials:

methyl (3S,4S,5E,7S,9R)-9-[(4-methoxybenzyl)oxy]-3,4,7-tri[(methoxymethyl)oxy]-5-decenoate

(4S,5S,8S,10R,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one