170438-03-6

Basic information

• Product Name: (S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one
• Synonyms: (S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one
• CAS NO: 170438-03-6
• Molecular Weight: 283.327
• Mol File: 170438-03-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one(170438-03-6)
• EPA Substance Registry System: (S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one(170438-03-6)

Safety Data

• Hazardous Substances Data: 170438-03-6(Hazardous Substances Data)

Upstream product

• 27513-44-6 N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester 
• 3978-80-1 Boc-Tyr-OH 
• 60-18-4 L-tyrosine 
• 100-39-0 benzyl bromide 
• 16679-94-0 N-[(phenylmethoxy)carbonyl]-L-tyrosine 
• 2130-96-3 O-benzyl-N-tert-butoxycarbonyl-L-tyrosine 
• 16652-64-5 O-benzyl-S-tyrosine 
• 66605-58-1 O-benzyl N-Boc-L-tyrosinol 
• 187332-12-3 (4S)-4-(4-hydroxybenzyl)-1,3-oxazolidin-2-one 
• 187521-90-0 (S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionic acid ethyl ester 
• 75-44-5 phosgene 
• 85803-44-7 (S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol 

Downstream Products

• 191105-59-6 (S)-N-propionyl-4-(4-hydroxybenzyl)oxazolidin-2-one 
• 191105-60-9 (S)-4-(4-Benzyloxy-benzyl)-3-propionyl-oxazolidin-2-one 
• 187332-12-3 (4S)-4-(4-hydroxybenzyl)-1,3-oxazolidin-2-one 

Relevant articles and documents

A practical synthesis of enantiopure (S)-4-(4-hydroxybenzyl)-oxazolidin-2-one

A high yielding four-step synthesis of enantiopure 4-(4-hydroxybenzyl)-oxazolidin-2-one (S)-1 from N-Boc-L-tyrosine is described. (S)-1 is a key intermediate for the preparation of a number of polymer supported Evans' oxazolidin-2-ones that have been employed previously for solid supported asymmetric synthesis.

N-Methylpyrrolidone Hydroperoxide/Cs2CO3 as an Excellent Reagent System for the Hydroxy-Directed Diastereoselective Epoxidation of Electron-Deficient Olefins

This report introduces N-methylpyrrolidone hydroperoxide (NMPOOH)/base as an excellent reagent system for hydroxy-directed syn selective epoxidation of electron-deficient olefins, characterized by high diastereoselectivity, short reaction times and remarkable chemoselectivity, especially in presence of oxidatively labile nitrogen or sulfur atoms. NMPOOH also proves efficient in the oxidation of electron-deficient aromatic aldehydes, in the removal of oxazolidinone chiral auxiliary, and in the functionalization of alkenes and alkynes, showing wide application potential. Something kinda HOO-: This report introduces N-methylpyrrolidone hydroperoxide/base as an excellent system for the hydroxy-directed syn-selective epoxidation of electron-deficient olefins, characterized by high diastereoselectivity, short reaction times and remarkable chemoselectivity, especially in the presence of oxidatively labile nitrogen or sulfur atoms.

An Improved Preparation of Oxazolidin-2-one Chiral Auxiliaries

Reduction of carbamate-blocked amino esters by lithium borohydride (made in situ from sodium borohydride and lithium iodide) forms chiral 4-substituted oxazolidin-2-ones directly. The presence of iodide in the reaction mixture appears to promote the cyclization of the intermediate alkoxyborohydride. This provides a route to these important chiral auxiliaries, employing less hazardous reagents and simpler reaction conditions than do most existing methods.