113000-77-4

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3R,4R,5R)-3,4,5-trihydroxypiperidine-2-carboxylic acid is used as a potential building block for the development of new drugs due to its unique stereochemistry and structural properties. Its presence in the biosynthesis of natural products indicates that it may have biological activity, making it a promising candidate for further research and analysis in drug discovery.
Used in Chemical Synthesis:
(2S,3R,4R,5R)-3,4,5-trihydroxypiperidine-2-carboxylic acid is used as a key intermediate in the synthesis of various chemical compounds. Its structural properties, including the piperidine ring and hydroxyl groups, make it a versatile component for creating complex molecules with potential applications in various industries.
Further research and analysis are required to fully understand the potential uses and properties of (2S,3R,4R,5R)-3,4,5-trihydroxypiperidine-2-carboxylic acid, as its current applications are based on its structural and biosynthetic characteristics.

Upstream product

• 1073610-92-0 (2S,3R,4R,5R)-1-tert-butyl 2-ethyl 3,4,5-trihydroxypiperidine-1,2-dicarboxylate 
• 1035405-79-8 2-amino-6-bromo-2,6-dideoxy-D-mannono-1,4-lactone hydrochloride 
• 226884-09-9 methyl 2,6-dideoxy-2,6-imino-D-mannonate 
• 121250-70-2 methyl 3,5-di-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside 
• 121195-22-0 methyl 3,5-di-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-D-mannofuranoside 
• 121195-21-9 methyl 3,5-di-O-benzyl-2,6-dideoxy-2,6-imino-D-mannofuranoside 
• 98260-67-4 methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside 
• 160147-89-7 methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate 
• 160147-87-5 methyl 2-benzyloxycarbonylamino-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate 
• 160147-88-6 methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-mannonate 
• 117462-55-2 methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate 
• 133473-08-2 methyl 3,4;5,6-di-O-isopropylidene-2-amino-2-deoxy-D-mannate 
• 160147-90-0 (2S,3R,4R,5R)-methyl 2,6-dideoxy-2,6-imino-3,4-O-isopropylidene-D-mannonate 
• 113000-78-5 N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-D-mannurono-1,4-lactone 

Relevant academic research and scientific papers

Regioselective intramolecular ring closure of 2-amino-6-bromo-2,6- dideoxyhexono-1,4-lactones to 5- or 6-membered iminuronic acid analogues: Synthesis of 1-deoxymannojirimycin and 2,5-dideoxy-2,5-imino-d-glucitol

1-Deoxymannojirimycin (8c) was synthesised from 2-amino-6-bromo-2,6- dideoxy-d-mannono-1,4-lactone (7) by intramolecular direct displacement of the C-6 bromine employing non-aqueous base treatment followed by reduction of the intermediate methyl ester. Li

Synthesis of both enantiomers of hydroxypipecolic acid derivatives equivalent to 5-azapyranuronic acids and evaluation of their inhibitory activities against glycosidases

We have synthesized 3-hydroxy- and 3,4,5-trihydroxypipecolic acid derivatives corresponding to 5-aza derivatives of uronic acids and evaluated their inhibitory activities against various glycosidases including β-glucuronidase. Compounds 4 and 5 were chosen as common intermediates for the synthesis of 3,4,5-trihydroxypipecolic acids and 3-hydroxypipecolic acids as well as for 3-hydroxybaikiain, a unique natural product isolated from a toxic mushroom. Cross aldol reaction of N-Boc-allylglycine derivative with acrolein followed by the ring-closing metathesis gave 4 and 5 as a mixture of diastereomers which could be separated by silica gel column chromatography. By employing lipase-catalyzed kinetic resolution, the synthesis of both l- and d-isomers of 3,4,5-trihydroxy- and 3-hydroxypipecolic acids was achieved. None of the compounds tested showed inhibitory activity against α- and β-glucosidases. On the other hand, l-23 and l-29 were found to have potent inhibitory activity against β-glucuronidase. In addition, it is interesting that some uronic-type azasugar derivatives showed moderate inhibitory activities against β-N-acetylglucosaminidase.

Simple Synthesis of (-)-Deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic Acid via Regioselective Hydrolysis

A short and efficient synthesis of (-)-deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is described with D-glucono-δ-lactone as chiral educt.Key transformations included selective cleavage of a terminal isopropylidene group with Dowex 50W-X8 (H+) and intramolecular nucleophilic amination.

A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S,3R,4R,5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE

Deoxymannojirimycin may be prepared in moderate amounts in an overall yield of 35percent in ten steps from diacetone glucose; the key step is formation of the piperidine ring by intramolecular nucleophilic displacement of a triflate at C-2 of a methyl glucofuranoside by a nitrogen function at C-6, irrespective of the anomeric configuration of the sugar.A synthesis of (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is reported.

SYNTHESIS OF DEOXYMANNOJIRIMYCIN FAGOMINE DEOXYNOJIRIMYCIN 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL 2S,3R,4R,5R-TRIHYDROXYPIPECOLIC ACID AND 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID FROM METHYL 3-O-BENZYL-2,6-DIDEOXY-2,6-IMINO-α-D-...

The value of methyl 3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside as a divergent intermediate for the preparation of polyhydroxylated piperidines is illustrated by the synthesis of deoxymannojirimycin (1,5-dideoxy-1,5-imino-D-mannitol), fagomine (1,5-imino-1,2,5-trideoxy-D-arabino-hexitol), deoxynojirimycin (1,5-dideoxy-1,5-imino-D-glucitol), 2-acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol, 2-acetamido-1,5-imino-1,2,5-trideoxy-D-glucitol, 2S,3R,4R,5R-trihydroxypipecolic acid and 2S,3R,4R,5S-trihydroxypipecolic acid.