105192-90-3

Basic information

• Product Name: ACHPA
• Synonyms: H-ACHPA-OH;CHA-STATINE;CYCLOHEXYLSTATINE;(3S,4S)-4-AMINO-3-HYDROXY-5-CYCLOHEXYL-PENTANOIC ACID;(3S,4S)-4-AMINO-5-CYCLOHEXYL-3-HYDROXY-PENTANOIC ACID;ACHPA;(3S,4S)-4-Amino-5-cyclohexyl-3-hydroxy-pent;(3S,4S)-4-Amino-5-cyclohexyl-3-hydroxy-pentanoic acid trifluoroacetate salt, 4-amino-5-cyclohexyl-2,4,5-trideoxy-L-threo-pentonic acid trifluoroacetate salt
• CAS NO: 105192-90-3
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 215.29
• Mol File: 105192-90-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ACHPA(CAS DataBase Reference)
• NIST Chemistry Reference: ACHPA(105192-90-3)
• EPA Substance Registry System: ACHPA(105192-90-3)

Safety Data

• Hazardous Substances Data: 105192-90-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ACHPA is used as a building block for the synthesis of various pharmaceutical compounds due to its high reactivity and versatility in chemical transformations.
Used in Agrochemical Industry:
ACHPA is used as a precursor in the synthesis of agrochemicals, contributing to the development of effective and targeted pest control solutions.
Used in Materials Science:
ACHPA is utilized in the production of advanced materials, taking advantage of its unique structure and reactivity to create innovative material properties.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
ACHPA is employed as a chiral auxiliary to facilitate asymmetric synthesis, enabling the production of enantiomerically pure compounds, which are essential in various applications, including pharmaceuticals and agrochemicals.
Used as a Ligand for Transition Metal Catalysis:
ACHPA serves as a ligand in transition metal catalysis, enhancing the efficiency and selectivity of catalytic reactions in organic synthesis.

Upstream product

• 70869-86-2 cyclohexylmethyl trifluoromethanesulfonate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 124947-31-5 N-(isopropoxycarbonyl)-L-phenylalanine methyl ester 
• 124995-02-4 (S)-N-(isopropoxycarbonyl)phenylalaninol 
• 128540-54-5 (S)-3-cyclohexyl-2-(isopropoxycarbonyl)aminopropanol 
• 128540-53-4 (S)-3-cyclohexyl-2-(isopropoxycarbonyl)aminopropanol 
• 63-91-2 L-phenylalanine 
• 126910-75-6 (S)-5-(cyclohexylmethyl)-2,4-pyrrolidinedione 
• 126910-82-5 (S)-α-<(3-ethoxy-1,3-dioxopropyl)amino>cyclohexanepropanoic acid, methyl ester 
• 126910-73-4 (S)-5-(cyclohexylmethyl)-2,5-dihydro-4-hydroxy-2-oxo-1H-pyrrole-3-carboxylic acid, ethyl ester 
• 126910-77-8 <4S(RS),5S>-5-(cyclohexylmethyl)-4-<(tetrahydro-2H-pyran-2-yl)oxy>-2-pyrrolidinone 
• 126910-76-7 (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone 
• 17193-39-4 methyl 3-cyclohexyl-L-alaninate hydrochloride 

Relevant articles and documents

A New Method for Hydroxymethylene Peptide Isostere Synthesis: Asymmetric Synthesis of Statine

The asymmetric synthesis of (-)-Statine is described.The key step of the synthesis involves the coupling of hemi-acetal 6 with the ketene silyl acetal of methyl acetate.

A highly stereoselective synthesis of (3S,4S)-statine and (3S,4S)-cyclohexylstatine

The title compounds, which are synthetic intermediates of renin inhibitors, could be prepared from (S)-leucine and (S)-phenylalanine, respectively, by employing highly stereoselective aldol reactions of O-methyl-O-trimethylsilyl ketene acetal with an (S)-

An expeditious synthesis of (3S,4S)-statine and (3S,4S)cyclohexylstatine

The title synthesis could be accomplished by employing highly stereoselective aldol reaction of O-methyl-O-trimethylsilyl ketene acetal with the (S)-α-amido aldehyde (2) in the presence of titanium (IV) chloride as a key step.

STEREOSPECIFIC SYNTHESIS OF S,S-STATINE AND ITS CONGENERS

Statine, (STA, 8) and its cyclohexyl analog (ACHPA, 9) are obtained by a stereospecific synthesis via tetramic acid chemistry.Amides of STA and ACHPA, useful for the synthesis of antihypertensive renin inhibitors, are prepared directly from the intermedia

Synthesis of Statine and Its Analogues

Statine, (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid, and its analogues were prepared from 5,6-anhydro-3-deoxy-1,2-O-isopropylidene-D-glucofuranose.The key step is the stereospecific reaction of the epoxy sugar with the Grignard reagent.