(4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal

Base Information

• Chemical Name: (4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal
• CAS No.: 207303-06-8
• Molecular Formula: C₂₅H₃₈O₆
• Molecular Weight: 434.573
• Mol file: 207303-06-8.mol

Synonyms:(4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal

Chemical Property of (4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal

There total 23 articles about (4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal 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: 82.0%

(E)-(4R,5S,6S)-7-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-4-methoxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hept-2-en-1-ol → (4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal (207303-06-8)

Guidance literature:

With N-methyl-2-indolinone; 4 A molecular sieve; tetrapropylammonium perruthennate; In dichloromethane; at 25 ℃; for 0.333333h;

DOI:10.1021/jo980754k

Reference yield:

(R)-2,2-diethyl-1,3-dioxolane-4-carboxaldehyde (120157-60-0) → (4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal (207303-06-8)

Guidance literature:

Multi-step reaction with 17 steps

1.1: ZnBr₂ / tetrahydrofuran; diethyl ether / 1 h / 0 °C

1.2: tetrahydrofuran; diethyl ether / 48 h / 0 °C

2.1: 96 percent / pyridine / CH₂Cl₂ / 17 h / 0 - 25 °C

3.1: 83 percent / LiHMDS; Me₃SiCl; Et₃N / tetrahydrofuran / 17.5 h / -100 - 25 °C

4.1: 38 percent / NaHCO₃; NBS / CCl₄ / 20 h / 20 °C

5.1: 86 percent / n-Bu₃SnH; AIBN / benzene / 16 h / Heating

6.1: 91 percent / LiAlH₄ / tetrahydrofuran / 22.5 h / -78 - 20 °C

7.1: 94 percent / DMAP; Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

8.1: 54 percent / Ph₃P; diethyl azodicarboxylate / benzene / 72 h / 20 °C

9.1: 96 percent / K₂CO₃ / methanol; diethyl ether; H₂O / 18 h / 20 °C

10.1: 99 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 3 h / 0 - 20 °C

11.1: 92 percent / TBAF*3H₂O / tetrahydrofuran / 1 h / 20 °C

12.1: 99 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.67 h / -78 - 20 °C

13.1: 92 percent / diethyl ether / 2 h / -78 - 25 °C

14.1: 93 percent / 4 Angstroem molecular sieves; NMO / TPAP / CH₂Cl₂ / 0.33 h / 25 °C

15.1: NaH / tetrahydrofuran / 0.5 h / 25 °C

15.2: 87 percent / tetrahydrofuran / 25 h / 25 - 60 °C

16.1: 96 percent / diisobutylaluminum hydride / diethyl ether; hexane / 2.5 h / -78 - 0 °C

17.1: 82 percent / 4 Angstroem molecular sieves; NMO / TPAP / CH₂Cl₂ / 0.33 h / 25 °C

With pyridine; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; chloro-trimethyl-silane; N-methyl-2-indolinone; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc dibromide; lithium hexamethyldisilazane; diethylazodicarboxylate; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1.1: transmetallation / 1.2: Addition / 2.1: Esterification / 3.1: Ireland-Claisen rearrangement / 4.1: Cyclization / 5.1: Dehalogenation / 6.1: Reduction / 7.1: silylation / 8.1: Mitsunobu reaction / 9.1: Hydrolysis / 10.1: Etherification / 11.1: desilylation / 12.1: Swern oxidation / 13.1: Grignard reaction / 14.1: Oxidation / 15.1: Metallation / 15.2: Horner-Wadsworth-Emmons reaction / 16.1: Reduction / 17.1: Oxidation;

DOI:10.1021/jo980754k

Reference yield:

(2R,3S,4R)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-3-methylpentane-1,4-diol (207303-17-1) → (4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal (207303-06-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 94 percent / DMAP; Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

2.1: 54 percent / Ph₃P; diethyl azodicarboxylate / benzene / 72 h / 20 °C

3.1: 96 percent / K₂CO₃ / methanol; diethyl ether; H₂O / 18 h / 20 °C

4.1: 99 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 3 h / 0 - 20 °C

5.1: 92 percent / TBAF*3H₂O / tetrahydrofuran / 1 h / 20 °C

6.1: 99 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.67 h / -78 - 20 °C

7.1: 92 percent / diethyl ether / 2 h / -78 - 25 °C

8.1: 93 percent / 4 Angstroem molecular sieves; NMO / TPAP / CH₂Cl₂ / 0.33 h / 25 °C

9.1: NaH / tetrahydrofuran / 0.5 h / 25 °C

9.2: 87 percent / tetrahydrofuran / 25 h / 25 - 60 °C

10.1: 96 percent / diisobutylaluminum hydride / diethyl ether; hexane / 2.5 h / -78 - 0 °C

11.1: 82 percent / 4 Angstroem molecular sieves; NMO / TPAP / CH₂Cl₂ / 0.33 h / 25 °C

With dmap; N-methyl-2-indolinone; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1.1: silylation / 2.1: Mitsunobu reaction / 3.1: Hydrolysis / 4.1: Etherification / 5.1: desilylation / 6.1: Swern oxidation / 7.1: Grignard reaction / 8.1: Oxidation / 9.1: Metallation / 9.2: Horner-Wadsworth-Emmons reaction / 10.1: Reduction / 11.1: Oxidation;

DOI:10.1021/jo980754k

upstream raw materials:

p-Methoxybenzyl bromide

(R)-2,2-diethyl-1,3-dioxolane-4-carboxaldehyde

4-Methoxybenzyl alcohol

(2R,3S,4R)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-3-methylpentane-1,4-diol