126260-84-2

Basic information

• Product Name: (4R,5R)-4-Methyl-5-(3-oxo-propyl)-oxazolidine-3-carboxylic acid cyclohexyl ester
• Synonyms: (4R,5R)-4-Methyl-5-(3-oxo-propyl)-oxazolidine-3-carboxylic acid cyclohexyl ester
• CAS NO: 126260-84-2
• Molecular Weight: 269.341
• Mol File: 126260-84-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4R,5R)-4-Methyl-5-(3-oxo-propyl)-oxazolidine-3-carboxylic acid cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R)-4-Methyl-5-(3-oxo-propyl)-oxazolidine-3-carboxylic acid cyclohexyl ester(126260-84-2)
• EPA Substance Registry System: (4R,5R)-4-Methyl-5-(3-oxo-propyl)-oxazolidine-3-carboxylic acid cyclohexyl ester(126260-84-2)

Safety Data

• Hazardous Substances Data: 126260-84-2(Hazardous Substances Data)

Upstream product

• 126260-83-1 (4R,5R)-5-(3-Benzyloxy-propyl)-4-methyl-oxazolidine-3-carboxylic acid cyclohexyl ester 
• 126260-82-0 (4R,5R)-5-(3-Hydroxy-propyl)-4-methyl-oxazolidine-3-carboxylic acid cyclohexyl ester 
• 126260-81-9 (4-Benzyloxy-1-vinyl-butoxymethyl)-carbamic acid cyclohexyl ester 
• 126260-80-8 (3RS)-6-benzyloxyhex-1-en-3-ol 
• 60794-21-0 cyclohexyl (N-hydroxymethyl)carbamate 
• 1124-54-5 carbamic acid cyclohexyl ester 

Downstream Products

• 126260-88-6 (4S,5S)-5-[2-(2-Dodecyl-[1,3]dioxolan-2-yl)-ethyl]-4-methyl-oxazolidine-3-carboxylic acid cyclohexyl ester 
• 126260-85-3 (4R,5R)-4-Methyl-5-(3-oxo-pentadecyl)-oxazolidine-3-carboxylic acid cyclohexyl ester 

Relevant articles and documents

STEREOSELECTIVE SYNTHESIS OF 3-HYDROXY-2,6-DIALKYLPIPERIDINES

A new method for stereoselektive synthesis of 3-hydroxy-2,6-dialkylpiperidine alkaloids is reported.The key trans-oxazolidine intermediate 8 was generated by mercuric ion-initiated cyclofunctionalization of an N-acylaminomethyl ether derivative of allylic alcohol 5 (6 -> 7).Racemic deoxocassine (3) was synthesized by addition of a C11 chain (8 -> 9), cleavage of the oxazolidine ring under basic conditions (9 -> 17), and reductive amination to generate the piperidine ring (17 -> 3).It was found that attempts to cleave the cyclohexyl carbamate group of oxazolidine 9 under acidic conditions resulted in rapid rearrangement to oxazolidinone 10 with inversion of stereochemistry at the O-substituted carbon.This oxazolidinone was converted to racemic isodeoxycassine (4) by ring cleavage (10 -> 14) and reductive amination.Treatment of oxazolidine 9 under strongly acidic conditions led to isolation of the 3-acetoxy-2,5-dialkylpiperidine 11, the product of an intramolecular Mannich reaction.