Technology Process of (3S,4R)-3-Hydroxy-4-[hydroxy-(6-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-3-hydroxymethyl-dihydro-furan-2-one
There total 1 articles about (3S,4R)-3-Hydroxy-4-[hydroxy-(6-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-3-hydroxymethyl-dihydro-furan-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 9 steps
1: 98 percent / tetrahydrofuran / 3 h / -75 °C
2: 92 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / -30 °C
3: 82 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0.5 h / -10 °C
4: 1.) osmium tetroxide; 2.) sodium periodate / 1.) room temp., 15 h, acetone-t.BuOH-H2O; 2.) room temp., 3 h, EtOAc-H2O
5: Ag2CO3-celite, / benzene / 0.75 h / Heating
6: Et3N / benzene / 4 h / Ambient temperature
7: DBU / benzene / 0.5 h / Ambient temperature
8: 4-methylmorpholine N-oxide / osmium tetroxide / acetone; 2-methyl-propan-2-ol; H2O / 12 h / Ambient temperature
9: n-Bu4NF, / tetrahydrofuran / 2 h / 0 °C
With
2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; silver carbonate;
osmium(VIII) oxide;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol; benzene;
DOI:10.1246/cl.1986.1771
- Guidance literature:
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Multi-step reaction with 7 steps
1: 59 percent / 10-camphorsulfonic acid / CH2Cl2 / 3 h / Ambient temperature
2: 85 percent / 2,6-lutidine / CH2Cl2 / 18 h / Ambient temperature
3: 99 percent / DIBAL / toluene / 1 h / -75 °C
4: 92 percent / 2-fluoro-1-methylpyridinium tosylate, Et3N / CH2Cl2 / 0.83 h / Ambient temperature
5: 50 percent / TrClO4, SnCl2, 4A molecular sive / diethyl ether / 2.5 h / 0 - 5 °C
6: 21 percent / n-Bu4NF / CH2Cl2 / 1.5 h / Ambient temperature
7: DMAP / 12 h / Ambient temperature
With
2,6-dimethylpyridine; dmap; Cl(3)HO4; 4A molecular sive; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; tin(ll) chloride;
In
diethyl ether; dichloromethane; toluene;
DOI:10.1246/bcsj.61.4361
