93086-26-1

Upstream product

• 100-42-5 styrene 
• 77940-37-5 5-bromo-4-phenyl-[1,3]dioxane 
• 103-64-0 bromostyrene 
• 2425-28-7 2-Bromo-1-phenylethanol 
• 108-24-7 acetic anhydride 
• 54299-23-9 (+/-)-threo-5-amino-4-phenyl-1,3-dioxane 

Downstream Products

• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 

Relevant academic research and scientific papers

STEREOSELECTIVE SYNTHESIS OF (+/-)-threo-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL

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 deg 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-nitrophe nyl)-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 dichloroacetylated in the known manner to give D-(-)-threo-2-dichloroacetylamino-1-(4-nitrophenyl)-1,3-propanediol (chloramphenicol).