123475-39-8

Basic information

• Product Name: (1S,2S)-1-hydroxy-1-phenyl-2-phthalimido-3-tosyloxy-propane
• Synonyms: (1S,2S)-1-hydroxy-1-phenyl-2-phthalimido-3-tosyloxy-propane
• CAS NO: 123475-39-8
• Molecular Weight: 451.5
• Mol File: 123475-39-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1S,2S)-1-hydroxy-1-phenyl-2-phthalimido-3-tosyloxy-propane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-1-hydroxy-1-phenyl-2-phthalimido-3-tosyloxy-propane(123475-39-8)
• EPA Substance Registry System: (1S,2S)-1-hydroxy-1-phenyl-2-phthalimido-3-tosyloxy-propane(123475-39-8)

Safety Data

• Hazardous Substances Data: 123475-39-8(Hazardous Substances Data)

Upstream product

• 85-44-9 phthalic anhydride 
• 123475-38-7 (1S,2S)-1(4-aminophenyl)-2-phthalimido-propane-1,3-diol 
• 1884-86-2 (1S,2S)-1-(4-nitrophenyl)-2-phthalimido-1,3-propanediol 
• 119-62-0 (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 123537-84-8 (1S,2S)-1-phenyl-2-phthalimido-propane-1,3-diol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 130873-80-2 (1S,2S)-1,3-dihydroxy-1-phenyl-prop-2-yl-ammonium chloride 
• 123537-85-9 (1S,2S)-1-acetoxy-1-phenyl-2-phthalimido-propane 
• 59686-10-1 1-phenyl-2-phthalimido-1-propanol 
• 2153-98-2 (-)-Norpseudoephedrine hydrochloride 
• 123475-40-1 (1S,2S)-1-acetoxy-1-phenyl-3-iodo-2-phthalimidopropane 

Relevant articles and documents

Application of the Mitsunobu reaction to ephedrines and some related amino alcohols. Aspects of intramolecular participation of the amino group

Inversion of configuration at the benzylic hydroxyl group of (1S,2S)-pseudoephedrine (2) to afford (1R,2S)-ephedrine is known to be a difficult process.The Mitsunobu reactions of 1 and 2 might offer a route to achieve such inversions.In fact Mitsunobu reactions on 1 and 2 are known to proceed via aziridines formed on intramolecular SN2 substitution by the amine functionality.The Mitsunobu reactions of N-methylated and N-benzylated ephedrines have been found to proceed via the corresponding aziridinium ions.These aziridinium ions can be opened (SN2 substitution) by nucleophiles like phthalimide and thiols.Intramolecular participation in 2 can be avoided by use of the tert-butyloxycarbonyl-(BOC) or benzyloxycarbonyl- (CBZ) protected derivatives.Mitsunobu reactions on these derivatives lead to inversion of configuration at the benzylic hydroxyl center.In contrast the BOC and CBZ derivatives of 1 are deprotected under Mitsunobu conditions.The Mitsunobu reactions of threo (1S,2S)-2-amino-1,3-propanediol have also been examined.An attempt to achieve protection by reaction with dimethylformamide dimethyl acetal led to the more substituted 2-oxazoline as established by X-ray crystallography.The desired inversion of configuration of the benzylic hydroxylic group was eventually achieved by protection of the amino substituent as the phthalimide and protection of the primary hydroxyl group as the tosylate.

(1S,2S)-2-Amino-1-aryl-propane-1,3-diols as Convenient Educts for the Synthesis of Homochiral (S,S)-Norpseudoephedrine

A convenient high yield synthesis of homochiral norpseudoephedrine starting from waste products of the chloramphenicol synthesis is described as an example of its utilization in chemical transformations.

A convenient synthesis of optically pure (S,S)-norpseudoephedrine

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