(3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal

Base Information

• Chemical Name: (3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal
• CAS No.: 185030-59-5
• Molecular Formula: C₂₃H₃₄O₇
• Molecular Weight: 422.519
• Mol file: 185030-59-5.mol

Synonyms:(3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal

Chemical Property of (3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal

There total 23 articles about (3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal 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: 84.0%

2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol (929118-00-3) → (3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal (185030-59-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -45 - 0 ℃;

DOI:10.1021/jo0623890

Reference yield:

(1E)-5-[(tert-butyldiphenylsilyl)oxy]-1-trimethylsilyl-1-penten-3-ol (851278-45-0) → (3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal (185030-59-5)

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: PPTS / CH₂Cl₂ / 20 °C

8.1: LiOH / methanol; tetrahydrofuran / 0.5 h / 20 °C

9.1: 134 mg / ethyldiisopropylamine / CH₂Cl₂ / 20 °C

10.1: 86 percent / Bu₄NF / tetrahydrofuran / 2 h / 40 °C

11.1: 84 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -45 - 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium hydroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; bromine; pyridinium p-toluenesulfonate; 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; methanol; diethyl ether; dichloromethane; 1.1: Sharpless epoxidation / 11.1: Swern oxidation;

DOI:10.1021/jo0623890

Reference yield:

(S)-1-chloro-2-hydroxy-5-trimethylsilyl-4-pentyne (148516-13-6) → (3S,4S,5E,7S,9R)-3.4-(dimethylmethylenedioxy)-9-(4-methoxybenzyloxy)-7-(methoxymethoxy)-5-decenal (185030-59-5)

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: PPTS / CH₂Cl₂ / 20 °C

10.1: LiOH / methanol; tetrahydrofuran / 0.5 h / 20 °C

11.1: 134 mg / ethyldiisopropylamine / CH₂Cl₂ / 20 °C

12.1: 86 percent / Bu₄NF / tetrahydrofuran / 2 h / 40 °C

13.1: 84 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -45 - 0 °C

With lithium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; pyridinium p-toluenesulfonate; 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; methanol; diethyl ether; dichloromethane; water; 13.1: Swern oxidation;

DOI:10.1021/jo0623890

upstream raw materials:

tert-Butyl-(2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethoxy)-dimethyl-silane

2-{(4S,5S)-5-[(E)-(3S,5R)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-hex-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol

(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

Downstream raw materials:

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