Technology Process of ((2R,3S,4S,5R,6R)-6-Acetyl-4-benzyloxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-acetaldehyde
There total 14 articles about ((2R,3S,4S,5R,6R)-6-Acetyl-4-benzyloxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-acetaldehyde which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: (-)-(Ipc)2BH / tetrahydrofuran / 336 h / -15 °C
1.2: 98 percent / H2O2; NaOH / tetrahydrofuran / 3 h
2.1: 96 percent / PCC; SiO2 / CH2Cl2 / 15 h / 20 °C
3.1: m-CPBA; NaHCO3 / CH2Cl2 / 15 h / 20 °C
4.1: 100 percent / TMSOTf / acetonitrile / -40 - -20 °C
5.1: 94 percent / BH3*THF / CH2Cl2 / 3 h / 0 °C
6.1: 100 percent / imidazole; DMAP / CH2Cl2 / 15 h / 20 °C
7.1: toluene / 15 h / 20 °C / ultrasound
7.2: 76 percent / aq. HCl / toluene / 0.5 h
8.1: 97 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
9.1: 89 percent / DBU / CH2Cl2 / 48 h / Heating
10.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
With
1H-imidazole; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; silica gel; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; diisopinocampheylborane; pyridinium chlorochromate;
In
tetrahydrofuran; dichloromethane; toluene; acetonitrile;
1.1: Addition / 1.2: Oxidation / 2.1: Oxidation / 3.1: Rearrangement / 4.1: Substitution / 5.1: Reduction / 6.1: Substitution / 7.1: Addition / 7.2: Hydrolysis / 8.1: Substitution / 9.1: Epimerization / 10.1: Oxidation;
DOI:10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 89 percent / DIBAH / tetrahydrofuran / 11 h / -78 °C
2.1: NaH / tetrahydrofuran
2.2: 99 percent / tetrahydrofuran / 16 h / Heating
3.1: (-)-(Ipc)2BH / tetrahydrofuran / 336 h / -15 °C
3.2: 98 percent / H2O2; NaOH / tetrahydrofuran / 3 h
4.1: 96 percent / PCC; SiO2 / CH2Cl2 / 15 h / 20 °C
5.1: m-CPBA; NaHCO3 / CH2Cl2 / 15 h / 20 °C
6.1: 100 percent / TMSOTf / acetonitrile / -40 - -20 °C
7.1: 94 percent / BH3*THF / CH2Cl2 / 3 h / 0 °C
8.1: 100 percent / imidazole; DMAP / CH2Cl2 / 15 h / 20 °C
9.1: toluene / 15 h / 20 °C / ultrasound
9.2: 76 percent / aq. HCl / toluene / 0.5 h
10.1: 97 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
11.1: 89 percent / DBU / CH2Cl2 / 48 h / Heating
12.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
With
1H-imidazole; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; silica gel; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; diisopinocampheylborane; pyridinium chlorochromate;
In
tetrahydrofuran; dichloromethane; toluene; acetonitrile;
1.1: Reduction / 2.1: Metallation / 2.2: Etherification / 3.1: Addition / 3.2: Oxidation / 4.1: Oxidation / 5.1: Rearrangement / 6.1: Substitution / 7.1: Reduction / 8.1: Substitution / 9.1: Addition / 9.2: Hydrolysis / 10.1: Substitution / 11.1: Epimerization / 12.1: Oxidation;
DOI:10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0
![1-[(2R,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone](/Databaselist/images/loading.webp)
