879899-01-1

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 2-(2-oxopropyl)-3-(phenylmethoxy)-, phenylmethyl ester, (2R,3S)-
• CAS NO: 879899-01-1
• Molecular Formula: C23H27NO4
• Molecular Weight: 381.472
• Mol File: 879899-01-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 2-(2-oxopropyl)-3-(phenylmethoxy)-, phenylmethyl ester, (2R,3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 2-(2-oxopropyl)-3-(phenylmethoxy)-, phenylmethyl ester, (2R,3S)-(879899-01-1)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 2-(2-oxopropyl)-3-(phenylmethoxy)-, phenylmethyl ester, (2R,3S)-(879899-01-1)

Safety Data

• Hazardous Substances Data: 879899-01-1(Hazardous Substances Data)

Usage

Molecular class

Piperidinecarboxylic acids

Molecular weight

353.41 g/mol

Structure

1-Piperidinecarboxylic acid derivative with a 2-(2-oxopropyl)-3-(phenylmethoxy)substituent

Ester group

Phenylmethyl ester

Stereochemistry

(2R,3S)configuration indicating the arrangement of functional groups around the chiral centers in the molecule

Potential applications

Pharmaceutical research and drug development due to unique structural features and potential biological activities.

Upstream product

• 501-53-1 benzyl chloroformate 
• 304665-09-6 (2R,3S)-benzyl 2-allyl-3-(benzyloxy) piperidine-1-carboxylate 
• 1450762-28-3 C₁₀H₁₆O₅ 
• 1450762-27-2 C₁₀H₁₄O₅ 
• 1450762-25-0 (S)-5-[(R)-1-hydroxy-2-(2-methyl-1,3-dioxolan-2-yl)ethyl]furan-2(5H)-one 
• 1450762-33-0 (2R,3S)-2-[(2-methyl-1,3-dioxolan-2-yl)methyl]piperidin-3-ol 
• 1450762-36-3 C₁₁H₁₈O₇S 
• 1450762-26-1 (S)-dihydro-5-[(R)-1-hydroxy-2-(2-methyl-1,3-dioxolan-2-yl)ethyl]furan-2(3H)-one 
• 1450762-35-2 benzyl (2R,3S)-3-(benzyloxy)-2-[(2-methyl-1,3-dioxolan-2-yl)methyl]piperidine-1-carboxylate 
• 1450762-34-1 benzyl (2R,3S)-3-hydroxy-2-[(2-methyl-1,3-dioxolan-2-yl)methyl]piperidine-1-carboxylate 
• 1450762-31-8 (5S,6R)-5-hydroxy-6-[(2-methyl-1,3-dioxolan-2-yl)methyl]piperidin-2-one 
• 1450762-29-4 (S)-5-[(R)-1-azido-2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-dihydrofuran-2(3H)-one 
• 1091605-50-3 (2R,3S)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 24159-07-7 febrifugine 
• 304665-12-1 (2R,3S)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester 
• 1203455-28-0 (2R,3S)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester 
• 17395-31-2 (+)-halofuginone didydrobromide 

Relevant articles and documents

Stereoselective total synthesis of all the stereoisomers of (+)- and (?)-febrifugine and halofuginone

A convenient method for the total synthesis of all the stereoisomers of febrifugine and halofuginone using D-arabinose and L-arabinose as the key starting materials is reported. Apart from the inherent stereocenters in these pentose sugars, the method utilizes the selective hydrogenolysis of the anomeric O-benzyl group, stereoselective Grignard reaction and Wacker oxidation as the key steps to obtain the important precursors for the total synthesis.

Dihydroxylation of vinyl sulfones: Stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone

(Chemical Equation Presented) The asymmetric dihydroxylation of amino-functionalized vinyl sulfone 19 has been used for the 3-step preparation of 3-hydroxylpiperidine 24 in 86% enantiomeric excess. This enantiomerically enriched building block was used then to synthesize the naturally occurring antimalarial alkaloid febrifugine 1 and its antiangiogenic analogue, halofuginone 3.

Stereocontrolled synthesis of a potent antimalarial alkaloid, (+)-febrifugine

A novel and stereocontrolled synthetic path to a potential antimalarial piperidine alkaloid, (+)-febrifugine, was established by employing a reductive deamination of a proline derivative with samarium diiodide, as a key step. A novel and stereocontrolled