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- W2005492034 abstract "Addition of hypobromic acid to styrene afforded styrene bromohydrin ( I ) which was dehydrated to ω-bromostyrene ( II ). Prince reaction of II with aqueous formaldehyde gave 5-bromo-4-phenyl-1,3-dioxane ( III ). The bromine atom in III was replaced with amino group by treatment with methanolic ammonia at 150°C and 6–8 MPa and the obtained threo -5-amino-4-phenyl-1,3-dioxane ( IVa ) was hydrolyzed to give (±)- threo -2-amino-1-phenyl-1,3-propanediol ( V ). Suitably chosen method of nitration converted the free base IVa or its N-acetyl derivative IVb into 5-amino-4-(4-nitrophenyl)-1,3-dioxane ( VIa ) or its N-acetyl derivative VIb which without isolation were hydrolyzed to threo -2-amino-1-(4-nitrophenyl)-1,3-propanediol ( VII ), isolated as hydrochloride. The liberated base was resolved into enantiomers and dichloracetylated in the known manner to give D-(-)- threo -2-dichloracetylamino-1-(4-nitrophenyl)-1,3-propanediol (chloramphenicol)." @default.
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- W2005492034 date "1989-01-01" @default.
- W2005492034 modified "2023-09-27" @default.
- W2005492034 title "Stereoselective synthesis of (±)-threo-2-amino-1-(4-nitrophenyl)-1,3-propanediol" @default.
- W2005492034 doi "https://doi.org/10.1135/cccc19892748" @default.
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