383418-30-2

Upstream product

• 100-42-5 styrene 
• 112-16-3 n-dodecanoyl chloride 
• 168154-77-6 (R)-2-amino-4-oxo-4-phenyl-butyric acid.HCl 
• 1434253-99-2 (R)-3-(tert-butyloxycarbonylamino)-4-hydroxy-1-phenylbutan-1-one 
• 53933-47-4 N-((1S)-1-phenylethyl)hydroxylamine 

Downstream Products

• 383418-32-4 Dodecanoic acid ((1R,3S)-3-hydroxy-1-methoxymethyl-3-phenyl-propyl)-amide 
• 383418-34-6 (1S,3R)-3-Amino-4-methoxy-1-phenyl-butan-1-ol 

Relevant academic research and scientific papers

A straightforward synthesis of the CERT inhibitor (1′R,3′S)-HPA-12

A straightforward synthesis of the CERT inhibitor HPA-12, (1′R,3′S)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide, is reported. The method requires only five synthetic steps from commercially available d-aspartic acid and leads to enantiopure HPA-12 in good overall yields.

Stereoselective Synthesis of a Ceramide Transporter Protein (CERT)-Dependent Ceramide-Trafficking Inhibitor, (1R,3S)-HPA-12, via Gold(I)-Catalyzed Cyclization of a Propargylic N-Hydroxylamine

A ceramide transporter protein (CERT)-dependent ceramide-trafficking inhibitor, HPA-12, is efficiently synthesized using gold(I)-catalyzed cyclization of a propargylic N-hydroxylamine, which is prepared via a stereoselective nitrone-alkyne addition reaction. The resulting 4-isoxazoline is converted into a syn-1,3-amino alcohol through stereoselective reduction and reductive ring opening.

A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12

A chemoenzymatic synthesis of the title compound has been developed using an efficient and highly enantioselective lipase-catalyzed acylation in a hydrophobic ionic liquid, [bmim][PF6], followed by a diastereoselective asymmetric dihydroxylatio

Synthesis of β-Amino Ketones by Addition of Aryl Methyl Ketones to Sulfinimines: Application to the Total Synthesis of HPA-12, Norsedamine, and Sedamine

Synthesis of β-sulfinamido ketones was accomplished by the addition of silyl enol ethers derived from arylmethyl ketones to chiral sulfinimines in excellent yield and selectivity. Application of the formed β-amino substituted ketones is exemplified in the total synthesis of sphingolipid HPA-12 and the sedamine alkaloids.

Organocatalytic route to enantioselective synthesis of ceramide trafficking inhibitor HPA-12

A new organocatalytic approach to the synthesis of ceramide trafficking inhibitor HPA-12 has been described starting from phenacyl bromide. The strategy involves chiral CBS reduction of γ-ketoester and proline-catalyzed α-amination reaction of aldehyde fo

Chelation controlled reduction of N-protected β-amino ketones toward the synthesis of HPA-12 and analogues

Diastereoselective reduction of N-protected β-amino ketones does not proceed effectively under the conditions used for chelation controlled reductions of N-alkyl β-amino ketones. A thorough analysis of various conditions required for the stereoselective r

Ruthenium-catalyzed asymmetric N -demethylative rearrangement of isoxazolidines and its application in the asymmetric total syntheses of (-)-(1 r,3 s)-hpa-12 and (+)-(1 s,3 r)-hpa-12

An asymmetric N-demethylative rearrangement of 1,2-isoxazolidines catalyzed by ruthenium is described. Enantioenriched syn-1,3-aminoalcohols as well as cis-1,3-oxazinanes, which are useful building blocks, can be efficiently prepared stereospecifically by this reaction in good yields, via the isoxazolidine intermediates in situ generated from a nitrone bearing a chiral auxiliary and styrenes. This asymmetric reaction was also applied in the asymmetric total syntheses of both (-)-(1R,3S)-HPA-12 and (+)-(1S,3R)-HPA-12.

Synthesis of potent CERT inhibitor HPA-12 featuring a tandem corey-link and intramolecular nucleophilic acyl substitution reaction

A novel preparation of the potent CERT protein inhibitor (1R,3S)-HPA-12 is described. The synthesis is accomplished in five steps from (S)-Wynberg lactone and features a diastereoselective tandem Corey-Link and intramolecular nucleophilic acyl substitution reaction in a key step. Georg Thieme Verlag Stuttgart · New York.

Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis

In response to Berke?'s report revising the stereochemistry of HPA-12, an important ceramide-trafficking inhibitor that was discovered and synthesized and its stereochemistry determined in 2001, the synthesis and the stereochemistry were reinvestigated. A large-scale synthetic method for HPA-12 based on a Zn-catalyzed asymmetric Mannich-type reaction in water was developed. Single crystals of HPA-12 for X-ray crystallographic analysis were obtained from ethyl propionate/n-hexane, and the stereochemistry was definitely determined to be 1R,3S, consistent with Berke?'s revised structure.

Expedient and practical synthesis of CERT-dependent ceramide trafficking inhibitor HPA-12 and its analogues

The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereoc