104863-92-5

Basic information

• Product Name: (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol
• Synonyms: (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol
• CAS NO: 104863-92-5
• Molecular Weight: 285.343
• Mol File: 104863-92-5.mol

Chemical Properties

• CAS DataBase Reference: (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol(104863-92-5)
• EPA Substance Registry System: (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol(104863-92-5)

Safety Data

• Hazardous Substances Data: 104863-92-5(Hazardous Substances Data)

Upstream product

• 54680-46-5 norephedrine 
• 14838-15-4 u-2-amino-1-phenylpropan-1-ol 
• 54064-02-7 benzyl [(1S)-1-methyl-2-oxo-2-phenylethyl]carbamate 
• 540-63-6 ethane-1,2-dithiol 
• 105140-27-0 (2S,4S,5R)-2-(2-Methoxycarbonyl-1-methyl-ethyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 105140-29-2 (2S,4S,5R)-2-(1-Methoxycarbonylmethyl-propyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 105140-32-7 (2S,4S,5R)-2-(1-Methoxycarbonylmethyl-butyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 105140-28-1 (2S,4S,5R)-2-(1-Methoxycarbonylmethyl-pentyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 492-41-1 (1R,2S)-norephedrine 
• 501-53-1 benzyl chloroformate 
• 105140-27-0 (2S,4S,5R)-2-((S)-2-Methoxycarbonyl-1-methyl-ethyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 105140-29-2 (2S,4S,5R)-2-((S)-1-Methoxycarbonylmethyl-propyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 105140-32-7 (2S,4S,5R)-2-((S)-1-Methoxycarbonylmethyl-butyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 105140-28-1 (2S,4S,5R)-2-((S)-1-Methoxycarbonylmethyl-pentyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 

Downstream Products

• 113323-06-1 (2S,4S,5R)-4-Methyl-5-phenyl-2-vinyl-oxazolidine-3-carboxylic acid benzyl ester 
• 120810-75-5 (2S,4S,5R)-2-((E)-3,3-Dimethoxy-propenyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 182051-48-5 (2S,4S,5R)-N-benzyloxycarbonyl-2-(2'-chloroethyl)-5-phenyl-4-methyl-1,3-oxazolidine 
• 16251-45-9 (S)-4-Methyl-5-phenyl-oxazolidin-2-one 
• 104863-88-9 (2S,4S,5R)-2-((1S,2R)-3-Benzyloxy-1,2-dihydroxy-propyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 104863-88-9 (2S,4S,5R)-2-((1R,2S)-3-Benzyloxy-1,2-dihydroxy-propyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 104863-89-0 (2S,4S,5R)-2-((1S,2S)-1,2-Dihydroxy-2-methoxycarbonyl-ethyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 104863-89-0 (2S,4S,5R)-2-((1R,2R)-1,2-Dihydroxy-2-methoxycarbonyl-ethyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 90-82-4 pseudoephedrine 
• 138058-66-9 (2R,4S,5R)-2-((S)-2-Benzyloxy-1-methyl-ethyl)-2,4-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 138058-63-6 (2R,4S,5R)-2-((R)-1-tert-Butylsulfanylcarbonyl-ethyl)-2,4-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 138058-72-7 (2R,4S,5R)-2-((R)-1-Methoxycarbonyl-ethyl)-2,4-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 138058-64-7 (2R,4S,5R)-2,4-Dimethyl-2-((R)-1-methyl-2-oxo-butyl)-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 138058-65-8 (2R,4S,5R)-2-((S)-2-Hydroxy-1-methyl-ethyl)-2,4-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 

Relevant articles and documents

Highly diastereoselective catalytic Meerwein-Ponndorf-Verley reductions

Very practical synthesis of ephedrine analogues in high yields and enantiopurity was realized by a highly diastereoselective Meerwein-Ponndorf- Verley (MPV) reduction of protected α-amino aromatic ketones using catalytic aluminum isopropoxide. The high anti selectivity resulted from the chelation of the nitrogen anion to the aluminum. In contrast, high syn selectivity was obtained with α-alkoxy ketones and other compounds via Felkin-Ahn control.

A General and Expeditious One-Pot Synthesis of Sulfoxides in High Optical Purity from Norephedrine-Derived Sulfamidites

A general and simple procedure for preparing any kind of enantiomerically enriched sulfoxide starting from norephedrine-derived N-benzyloxycarbonylsulfamidite 3a is reported. After one-pot reaction of 3a with RMgX, HBF4, and R'MgX, a variety of sulfoxides 6 are obtained in ee usually higher than 93% and isolated yields ranging between 50 and 78%. The obtained configuration is tunable by simply electing the order of the addition of the reagents.

An enantioselective synthesis of (1S,2S)-pseudoephedrine

Synthesis of (1S,2S)-pseudoephedrine is described via reduction of an alanine-derived oxazolidinone followed by treating with phenyl magnesium bromide and chemoselective N-methylation in an efficient and practical manner. (C) 2000 Elsevier Science Ltd.

Preparation of 2-oxazolidinones by intramolecular nucleophilic substitution

Treatment of N-alkoxycarbonyl, N-benzyl protected β-amino alcohols with triphenylphosphine and hexachloroethane in 1,2-dichloroethane induces cyclization to 2-oxazolidinones, which are formed by intramolecular attack with inversion of configuration at the secondary alcohol. In contrast, mono N-substituted alkyl carbamates undergo chlorination under the same conditions.

Highly stereoselective acetylations via norephedrine derived oxazolidines

Norephedrine derived 2-methoxy-2-methyl oxazolidine 2 is an efficient stereoselective acetylating agent in reactions with stereogenic silylenolethers and silylketenethiolacetals. Moderate selectivity is also obtained upon acetylation of crotyltin reagents

ALUMINUM-MEDIATED ONE-POT CONVERSION OF α-AMINO ACID ESTERS TO THREO 2-AMINO ALCOHOLS WITH HIGH DIASTEREOSELECTIVITY

Reduction of N-Cbz α-amino acid esters with DIBAl-H, followed by treatment with Grignard reagent in a one-pot manner gave the corresponding threo 2-amino alcohols with high diastereoselectivity without racemization. KEYWORDS 2-amino alcohol; α-amino acid ester; DIBAL-H reduction; α-amino aldehyde; chelation controll; diastereoselective synthesis; one-pot synthesis

ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION OF CUPRATES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE. ENANTIOSELECTIVE SYNTHESIS OF 2-ALKYL-4-BENZYLOXYBUTANAL AND 2-ALKYL-4-OXOPENTANAL.

Cuprate reagents in the presence of trimethylchlorosilane add with excellent Π-face selectivity and yield to α,β-unsaturated ketone and aldehyde bearing in γ-position a masked aldehyde represented by the C-2 of a norephedrine-derived oxazolidine.The title

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A NEW FACILE DIASTEREOCONVERSION OF 2-AMINO ALCOHOLS INVOLVING A NOVEL CYCLOCARBAMATION

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Allylic Stereocenter Directed Asymmetric Conjugate Addition. Enantioselective Synthesis of 3-Alkylsuccinaldehydic Acid Methyl Esters

Cuprate reagents add to ester 2 with excellent ?-face selectivity (>=95:5) and furnish the title compounds in high enantiomeric excess after removal of the chiral auxiliary.