Technology Process of (3S,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one
There total 8 articles about (3S,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
N-fluorobis(benzenesulfon)imide; lithium hexamethyldisilazane;
In
tetrahydrofuran;
at -78 ℃;
for 1.5h;
diastereoselective reaction;
DOI:10.1021/ja502205q
- Guidance literature:
-
Multi-step reaction with 5 steps
1: copper dichloride; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid / ethyl acetate / 24 h / -30 °C / Molecular sieve
2: titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate / dichloromethane / 16 h / -40 °C / Inert atmosphere
3: zinc; water; trifluoroacetic acid / toluene / 32 h / 20 °C
4: dmap; 1H-imidazole / dichloromethane / 24 h / 20 °C
5: N-fluorobis(benzenesulfon)imide; lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C
With
1H-imidazole; dmap; titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; water; N-fluorobis(benzenesulfon)imide; trifluoroacetic acid; copper dichloride; lithium hexamethyldisilazane; zinc;
In
tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
2: |Mukaiyama Aldol Addition;
DOI:10.1021/ja502205q
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C
1.2: 16 h / 20 °C
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 20 °C
3.1: copper dichloride; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid / ethyl acetate / 24 h / -30 °C / Molecular sieve
4.1: titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate / dichloromethane / 16 h / -40 °C / Inert atmosphere
5.1: zinc; water; trifluoroacetic acid / toluene / 32 h / 20 °C
6.1: dmap; 1H-imidazole / dichloromethane / 24 h / 20 °C
7.1: N-fluorobis(benzenesulfon)imide; lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C
With
1H-imidazole; dmap; titanium(IV) dichlorodiisopropylate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; water; sodium hydride; N-fluorobis(benzenesulfon)imide; trifluoroacetic acid; copper dichloride; lithium hexamethyldisilazane; zinc;
In
tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;
4.1: |Mukaiyama Aldol Addition;
DOI:10.1021/ja502205q
