604789-37-9

Basic information

• Product Name: 3,4-Pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, (2R,3R,4R)-rel- (9CI)
• Synonyms: 3,4-Pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, (2R,3R,4R)-rel- (9CI)
• CAS NO: 604789-37-9
• Molecular Formula: C12H17NO3
• Molecular Weight: 223.26828
• Product Categories: ALCOHOL
• Mol File: 604789-37-9.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,4-Pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, (2R,3R,4R)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, (2R,3R,4R)-rel- (9CI)(604789-37-9)
• EPA Substance Registry System: 3,4-Pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, (2R,3R,4R)-rel- (9CI)(604789-37-9)

Safety Data

• Hazardous Substances Data: 604789-37-9(Hazardous Substances Data)

Upstream product

• 228396-56-3 {(1R)-1-(N-tert-butoxycarbonylamino)-1-deoxy-1-(p-methoxybenzyl)-2,3-O-isopropylidene-4-chloro-L-threitol} 
• 478623-19-7 ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 478623-18-6 ethyl (2R,3S,4R)-4-(tert-butoxycarbonyl)amino-2,3-dihydroxy-5-(4-methoxyphenyl)pentanoate 
• 478623-20-0 (1R,4R,5R)-1-[N-(tert-butoxycarbonyl)]-1-(5-bromomethyl-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxyphenyl)ethan-1-amine 
• 478623-17-5 ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate 
• 120349-75-9 (2R)-2-(tert-butoxycarbonyl)amino-3-(4-methoxyphenyl)propan-1-ol 
• 139183-60-1 [(R)-1-Formyl-2-(4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 94790-24-6 (2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester 
• 606147-97-1 (2S,3S,4R)-1-O-benzyl-4-(benzylamino)-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 
• 293314-35-9 (2S,3S,4R)-4-(benzylamino)-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 
• 228396-51-8 {(1R)-1-(N-benzyl-N-hydroxyamino)-1-deoxy-1-(p-methoxybenzyl)-4-O-benzyl-2,3-O-isopropylidene-L-threitol} 
• 165877-97-4 (2R,3S,4S)-N-benzyl-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 23006-20-4 (3R,4S,5R)-N-Benzyl-3,4-dihydroxy-5-p-anisyl-pyrrolidon-2 
• 112463-98-6 Acetic acid (3R,4S,5R)-4-hydroxy-5-(4-methoxy-benzyl)-2-oxo-pyrrolidin-3-yl ester 

Relevant articles and documents

Total Synthesis of (-)-Anisomycin

Antibiotic (-)-anisomycin was synthesized starting from D-tyrosine using the addition of electrogenerated dichloro-(methoxycarbonyl)methyl anion to aldehyde 2 as a key reaction.

A common strategy towards the synthesis of 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars

A strategy towards the synthesis of three different target molecules, namely 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars, molecules of potential biological and medicinal significance, is reported from a common amino-vicinal diol intermediate derived from tri-O-benzyl-D-glucal. Construction of the key pyrrolidine ring present in 1,4-dideoxy-1,4-imino-L-xylitol and (+)-anisomycin was a consequence of thermodynamically driven concomitant intramolecular nucleophilic addition reaction of the amino group to the resultant aldehyde obtained by oxidative cleavage of the amino-vicinal diol. Alternatively, double nucleophilic substitution on an amino-diol, after mesylation, with various amines delivered amino-substituted piperidine iminosugars in good yields.

A facile and stereoselective synthesis of the C-2 epimer of (+)-deacetylanisomycin

A short, simple and efficient synthesis of the C-2 epimer of (+)-deacetylanisomycin starting from d-mannitol, utilizing an epoxide opening with a Grignard reagent and acid catalysed unusual intramolecular 5-endo-tet cyclization as key steps has been repor

A new approach to (+)-anisomycin

An efficient approach to enantiomerically pure (+)-deacetylanisomycin 2a and a formal synthesis of (+)-anisomycin 2 (11% overall yield in 10 steps) have been achieved through simple and good yielding reactions, starting from 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol 3. Grignard reaction and intramolecular cyclisation reactions are key steps in the strategy.