Technology Process of (Z)-4-[(2R,6R)-6-((S)-4-Formyl-2-methyl-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester
There total 16 articles about (Z)-4-[(2R,6R)-6-((S)-4-Formyl-2-methyl-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
N,N-dimethyl(methylene)ammonium chloride; (Z)-4-[(2R,6R)-6-((S)-2-Methyl-5-oxo-pentyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 2,4-dimethoxy-benzyl ester;
In
dichloromethane;
for 48h;
With
triethylamine;
DOI:10.1016/S0040-4039(00)02116-X
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 80 percent / PDC / dimethylformamide / 20 °C
2.1: ozone / methanol / -78 °C
2.2: 82 percent / NaBH4
3.1: 89 percent / DMAP; imidazole / dimethylformamide / 10 h / 20 °C
4.1: 85 percent / DIBAL / CH2Cl2 / 1.5 h / -78 °C
5.1: 80 percent / (S)-BINOL; Ti(Oi-Pr)4
6.1: 83 percent / Pd(OAc)2 / acetonitrile / 20 h / Heating
7.1: 85 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 36 h / 20 °C
8.1: 78 percent / EtOAc; LiClO4
9.1: 80 percent / KHMDS; 18-crown-6 / tetrahydrofuran / -78 °C
10.1: 91 percent / HF-pyridine / tetrahydrofuran
11.1: (COCl2); DMSO / -78 °C
11.2: 90 percent / Et3N / -78 - 20 °C
12.1: CH2Cl2 / 48 h
12.2: 84 percent / Et3N
With
1H-imidazole; titanium(IV) isopropylate; phosgene; dmap; palladium diacetate; dipyridinium dichromate; Grubbs catalyst first generation; 18-crown-6 ether; (S)-[1,1']-binaphthalenyl-2,2'-diol; lithium perchlorate; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; dimethyl sulfoxide; ethyl acetate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
8.1: Ferrier rearrangement;
DOI:10.1016/S0040-4039(00)02116-X
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: ozone / methanol / -78 °C
1.2: 82 percent / NaBH4
2.1: 89 percent / DMAP; imidazole / dimethylformamide / 10 h / 20 °C
3.1: 85 percent / DIBAL / CH2Cl2 / 1.5 h / -78 °C
4.1: 80 percent / (S)-BINOL; Ti(Oi-Pr)4
5.1: 83 percent / Pd(OAc)2 / acetonitrile / 20 h / Heating
6.1: 85 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 36 h / 20 °C
7.1: 78 percent / EtOAc; LiClO4
8.1: 80 percent / KHMDS; 18-crown-6 / tetrahydrofuran / -78 °C
9.1: 91 percent / HF-pyridine / tetrahydrofuran
10.1: (COCl2); DMSO / -78 °C
10.2: 90 percent / Et3N / -78 - 20 °C
11.1: CH2Cl2 / 48 h
11.2: 84 percent / Et3N
With
1H-imidazole; titanium(IV) isopropylate; phosgene; dmap; palladium diacetate; Grubbs catalyst first generation; 18-crown-6 ether; (S)-[1,1']-binaphthalenyl-2,2'-diol; lithium perchlorate; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; dimethyl sulfoxide; ethyl acetate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
7.1: Ferrier rearrangement;
DOI:10.1016/S0040-4039(00)02116-X
