178113-66-1

Upstream product

• 178267-25-9 (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid 
• 74-88-4 methyl iodide 
• 223908-36-9 4-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester 
• 116949-67-8 (2S,3S)-2-azido-1-phenyl-butane-3,4-diol 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 223908-35-8 (3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 936226-69-6 (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester 
• 100-39-0 benzyl bromide 
• 229981-33-3 tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate 
• 72155-49-8 N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid 
• 72155-47-6 N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester 
• 220931-41-9 (S)-4-Benzyl-5-[1-ethoxycarbonyl-meth-(E)-ylidene]-oxazolidine-3-carboxylic acid benzyl ester 
• 223908-34-7 (4S,3R)-4-(benzyloxycarbonyl-methylamino)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester 

Downstream Products

• 185208-62-2 (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester 
• 178113-67-2 (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester 
• 185208-63-3 (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]oxy}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate 
• 676525-98-7 (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester 
• 314030-97-2 (1R)-1-[(1S)-2-({(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl}oxy)-1-methyl-2-oxoethyl]octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate 
• 238753-91-8 (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]oxy}-1-methyl-2-oxoethyl)octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate 
• 238753-90-7 (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid 
• 159542-04-8 (-)-hapalosin 
• 185208-61-1 (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid benzyl ester 

Relevant academic research and scientific papers

An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (?)-hapalosin

A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P1 = TBS, P2 = H) has been developed through a stereoselective tandem Barbier process of (R,SRS)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used to prepare a variety of substituted (3R,4S)-statines 2. In addition, two bioactive natural products of (+)-preussin 4 and hapalosin 5 were effectively synthesized through this stereoselective tandem Barbier process.

A stereocontrolled synthesis of hapalosin

A facile synthetic method for two components of hapalosin, that is, β-hydroxy-γ-amino acid and β-hydroxy acid, has been established by utilizing chiral building blocks efficiently resolved in a lipase-catalyzed transesterification. Furthermore, the synthe

A novel protocol for N-methyl-γ-amino-β-hydroxy acids from oxazolidinones

A new two step methodology for N-methyl-γ-amino-β-hydroxy acids from oxazolidinones is described.

A totally stereocontrolled route to N-methyl-γ-amino-β-hydroxy acids: Asymmetric synthesis of the amino acid component of hapalosin

A new approach to the synthesis of N-methyl-γ-amino-β-hydroxy acids, compounds that are essential components of several depsipeptides exhibiting highly interesting therapeutic profiles, is presented. Relevant steps in the synthetic sequence involve the totally stereoselective preparation of a protected aminoalkyl epoxide from a highly enantiopure 2,3-epoxy alcohol, efficient N-methylation and three-step conversion to the desired N-methyl amino acid. The method is exemplified by the enantioselective synthesis of (3R,4S)-4-(N-methylamino)-3-hydroxy-5-phenylpentanoic acid in two differently protected forms.

Total synthesis of the multidrug-resistance reversing agent hapalosin

Hapalosin, a new reversing MDR agent, has been synthesized by macrolactamisation of a linear precursor 2 derived from the coupling of a β-hydroxy γ-aminoacid 3 and two hydroxy-esters 4 and 5. The aminoacid 3 was stereoselectively obtained by opening of an anti β-aminoepoxide while the 3-hydroxyacid 4 was prepared by condensation of a lithium compound with (R)-2-phenyl-propanal followed by oxidation of the phenyl group.

Chemical study on hapalosin, a cyclic depsipeptide possessing multidrug resistance reversing activities: Synthesis, structure and biological activity

Hapalosin 1 possessing a multidrug resistance reversing activity, has been synthesized from the corresponding hydroxy acids A, C and γ-amino acid B. The stereochemistry of the natural product 1 and N-demethylhapalosin 11 is discussed by means of spectroscopic manner as well as molecular modeling studies. Biological evaluation of 1 and 11 indicated that a cis-amide function is a crucial factor for the MDR reversing activity.

Synthetic study on hapalosin, a cyclic depsipeptide possessing multidrug resistance reversing activities

Hapalosin possessing a multidrug resistance reversing activity, has been synthesized from the corresponding hydroxy acids and γ-amino acids. The stereochemistry of the natural product and related derivatives is discussed.