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

Base Information

Chemical Name:(2R,3S,4S)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-4-[(4-methoxyphenyl)methoxy]-3-methylpentanal
CAS No.:207303-19-3
Molecular Formula:C₂₂H₃₄O₆
Molecular Weight:394.508
Hs Code.:

Synonyms:(2R,3S,4S)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-4-[(4-methoxyphenyl)methoxy]-3-methylpentanal

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

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

There total 18 articles about (2R,3S,4S)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-4-[(4-methoxyphenyl)methoxy]-3-methylpentanal 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: 99.0%

: 207303-03-5
(2R,3S,4S)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-4-[(4-methoxyphenyl)methoxy]-3-methylpentan-1-ol

: 207303-19-3
(2R,3S,4S)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-4-[(4-methoxyphenyl)methoxy]-3-methylpentanal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(98)00268-8

Reference yield:

: 120157-60-0
(R)-2,2-diethyl-1,3-dioxolane-4-carboxaldehyde

: 207303-19-3
(2R,3S,4S)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-4-[(4-methoxyphenyl)methoxy]-3-methylpentanal

Guidance literature:: Multi-step reaction with 12 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

With pyridine; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; chloro-trimethyl-silane; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc dibromide; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; 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;
DOI:10.1021/jo980754k

Reference yield:

: 214462-03-0
1-[(1R)-3,3-diethyl-2,4-dioxolanyl]but-2-yn-1-one

: 207303-19-3
(2R,3S,4S)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-4-[(4-methoxyphenyl)methoxy]-3-methylpentanal

Guidance literature:: Multi-step reaction with 15 steps

1: 389 mg / (R)-Alpine borane / tetrahydrofuran / 40 h / 20 °C

2: 97 percent / DMAP; Et₃N / 18.3 h / 0 - 20 °C

3: 70 percent / KH₂PO₄; air / porcine pancreatic lipase (EC 3.1.1.3) / H₂O / 6.5 h / 23 °C / pH 6.0

4: 98 percent / LiAlH₄ / tetrahydrofuran / 20.5 h / 0 - 20 °C / Heating

5: 96 percent / pyridine / CH₂Cl₂ / 17 h / 0 - 25 °C

6: 83 percent / LiHMDS; Me₃SiCl; Et₃N / tetrahydrofuran / 17.5 h / -100 - 25 °C

7: 38 percent / NaHCO₃; NBS / CCl₄ / 20 h / 20 °C

8: 86 percent / n-Bu₃SnH; AIBN / benzene / 16 h / Heating

9: 91 percent / LiAlH₄ / tetrahydrofuran / 22.5 h / -78 - 20 °C

10: 94 percent / DMAP; Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

11: 54 percent / Ph₃P; diethyl azodicarboxylate / benzene / 72 h / 20 °C

12: 96 percent / K₂CO₃ / methanol; diethyl ether; H₂O / 18 h / 20 °C

13: 99 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 3 h / 0 - 20 °C

14: 92 percent / TBAF*3H₂O / tetrahydrofuran / 1 h / 20 °C

15: 99 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.67 h / -78 - 20 °C

With pyridine; dmap; potassium dihydrogenphosphate; N-Bromosuccinimide; lithium aluminium tetrahydride; chloro-trimethyl-silane; oxalyl dichloride; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; air; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; porcine pancreatic lipase (EC 3.1.1.3); In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Acetylation / 3: Hydrolysis / 4: Reduction / 5: Esterification / 6: Ireland-Claisen rearrangement / 7: Cyclization / 8: Dehalogenation / 9: Reduction / 10: silylation / 11: Mitsunobu reaction / 12: Hydrolysis / 13: Etherification / 14: desilylation / 15: Swern oxidation;
DOI:10.1021/jo980754k