Technology Process of (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenal
There total 10 articles about (2Z,4R,6R)-4-(tert-butyldimethylsilyl)oxy-7-(4-methoxybenzyl)oxy-6-(triethylsilyl)oxy-2-heptenal which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
Dess-Martin periodane;
In
dichloromethane;
at 25 ℃;
for 1h;
DOI:10.1021/ja010195q
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 95 percent / BF3*OEt2 / cyclohexane; CH2Cl2 / 25 °C
2: DIBAL-H / CH2Cl2; toluene / 1.5 h / -78 °C
3: 73 percent / MsCl; Et3N; DMAP / CH2Cl2 / 2.5 h / Heating
4: (DHQD)2AQN; K2OsO2(OH)4; K3Fe(CN)6 / K2CO3; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 2 °C
5: Et3N / CH2Cl2 / 0.5 h / -78 °C
6: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C
7: 95 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C
8: 90 percent / DIBAL-H / toluene; hexane / 0.33 h / -20 °C
9: Dess-Martin periodinane / CH2Cl2 / 1 h / 25 °C
With
dmap; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; acetonitrile; potassium hexacyanoferrate(III);
methanesulfonamide; potassium carbonate;
In
tetrahydrofuran; hexane; dichloromethane; cyclohexane; water; toluene; tert-butyl alcohol;
4: Sharpless assymetric dihydroxylation / 9: Dess-Martin oxidation;
DOI:10.1021/ja010195q
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 95 percent / BF3*OEt2 / cyclohexane; CH2Cl2 / 25 °C
2: DIBAL-H / CH2Cl2; toluene / 1.5 h / -78 °C
3: 73 percent / MsCl; Et3N; DMAP / CH2Cl2 / 2.5 h / Heating
4: (DHQD)2AQN; K2OsO2(OH)4; K3Fe(CN)6 / K2CO3; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 2 °C
5: Et3N / CH2Cl2 / 0.5 h / -78 °C
6: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C
7: 95 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C
8: 90 percent / DIBAL-H / toluene; hexane / 0.33 h / -20 °C
9: Dess-Martin periodinane / CH2Cl2 / 1 h / 25 °C
With
dmap; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; acetonitrile; potassium hexacyanoferrate(III);
methanesulfonamide; potassium carbonate;
In
tetrahydrofuran; hexane; dichloromethane; cyclohexane; water; toluene; tert-butyl alcohol;
4: Sharpless assymetric dihydroxylation / 9: Dess-Martin oxidation;
DOI:10.1021/ja010195q
