Technology Process of (2E,7E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal
There total 20 articles about (2E,7E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 71 percent / 4 Angstroem molecular sieves / chiral Cr(III) catalyst
2.1: Et3SiH; BF3*OEt2 / CH2Cl2
2.2: 72 percent / HCl / CH2Cl2; methanol
3.1: 80 percent / (COCl)2; DMSO; Et3N
4.1: (c-Hex)2BCl; Et3N / diethyl ether / -78 °C
4.2: H2o2
4.3: 87 percent / MsCl; Et3N / CH2Cl2
5.1: 100 percent / Zn(BH4)2 / diethyl ether / -40 °C
6.1: 26-lutidine
7.1: TBAF; AcOH
With
2,6-dimethylpyridine; triethylsilane; zinc(II) tetrahydroborate; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; triethylamine;
chiral Cr(III) catalyst;
In
diethyl ether; dichloromethane;
1.1: hetero-Diels-Alder reaction / 3.1: Swern oxidation / 8.1: Dess-Martin oxidation;
DOI:10.1021/ol010150u
- Guidance literature:
-
Multi-step reaction with 15 steps
1.1: TfOH / diethyl ether
2.1: LiAlH4 / tetrahydrofuran
3.1: iPr2NEt; LiCl / acetonitrile
4.1: DIBAL / CH2Cl2 / -78 °C
5.1: imidazole / CH2Cl2
6.1: p-TsOH / methanol
7.1: (c-Hex)2BCl; Et3N / diethyl ether / -78 °C
7.2: H2o2
7.3: 87 percent / MsCl; Et3N / CH2Cl2
8.1: 100 percent / Zn(BH4)2 / diethyl ether / -40 °C
9.1: 26-lutidine
10.1: TBAF; AcOH
With
1H-imidazole; 2,6-dimethylpyridine; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; trifluorormethanesulfonic acid; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;
3.1: Dess-Martin oxidation / 4.1: Horner-Wadsworth-Emmons olefination / 8.1: Swern oxidation / 9.1: Grignard reaction / 10.1: Swern oxidation / 15.1: Dess-Martin oxidation;
DOI:10.1021/ol010150u
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: (c-Hex)2BCl; Et3N / diethyl ether / -78 °C
1.2: H2o2
1.3: 87 percent / MsCl; Et3N / CH2Cl2
2.1: 100 percent / Zn(BH4)2 / diethyl ether / -40 °C
3.1: 26-lutidine
4.1: TBAF; AcOH
With
2,6-dimethylpyridine; zinc(II) tetrahydroborate; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; acetic acid; triethylamine;
In
diethyl ether;
5.1: Dess-Martin oxidation;
DOI:10.1021/ol010150u