74644-88-5

Usage

InChI:InChI=1/C5H9NO4/c7-2-1-6-3(4(2)8)5(9)10/h2-4,6-8H,1H2,(H,9,10)/t2-,3+,4+/m1/s1

Upstream product

• 17645-37-3 (2RS)-hydroxymethyl-1-tosylpyrrolidine-(3SR,4RS)-diol 
• 138228-39-4 (3S,4S)-3,4-dibenzoyloxy-2-cyanopyrrolidine 
• 131053-16-2 methyl 5-azido-3-O-benzyl-5-deoxy-α-D-xylofuranoside 
• 131053-28-6 methyl 5-azido-3-O-benzyl-5-deoxy-β-D-xylofuranoside 
• 131053-18-4 methyl 3-O-benzyl-2,5-dideoxy-2,5-imino-α-D-lyxofuranoside 
• 131102-04-0 methyl 3-O-benzyl-2,5-dideoxy-2,5-imino-β-D-lyxofuranoside 
• 131053-19-5 3-O-benzyl-N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-D-lyxose 
• 131053-14-0 3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-xylo-furanose 
• 131053-15-1 5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 
• 34370-91-7 3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 105016-02-2 ((3S,4R,5S)-5-Bromomethyl-4-hydroxy-2-oxo-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester 
• 101623-96-5 (2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-pent-4-enoic acid 
• 792876-67-6 (3S,4R,5S)-3-Amino-5-bromomethyl-4-hydroxy-dihydro-furan-2-one 
• 78138-86-0 2,5-dibromo-2,5-dideoxy-D-xylono-1,4-lactone 

Downstream Products

• 138228-51-0 (2S,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine 
• 138228-52-1 (2R,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine 

Relevant academic research and scientific papers

Structural essentials for β-: N -acetylhexosaminidase inhibition by amides of prolines, pipecolic and azetidine carboxylic acids

This paper explores the computer modelling aided design and synthesis of β-N-acetylhexosaminidase inhibitors along with their applicability to human disease treatment through biological evaluation in both an enzymatic and cellular setting. We investigated the importance of individual stereocenters, variations in structure-activity relationships along with factors influencing cell penetration. To achieve these goals we modified nitrogen heterocycles in terms of ring size, side chains present and ring nitrogen derivatization. By reducing the inhibitor interactions with the active site down to the essentials we were able to determine that besides the established 2S,3R trans-relationship, the presence and stereochemistry of the CH2OH side chain is of crucial importance for activity. In terms of cellular penetration, N-butyl side chains favour cellar uptake, while hydroxy- and carboxy-group bearing sidechains on the ring nitrogen retarded cellular penetration. Furthermore we show an early proof of principle study that β-N-acetylhexosaminidase inhibitors can be applicable to use in a potential anti-invasive anti-cancer strategy.

The conversion of pentoses to 3,4-dihydroxyprolines

The synthesis of two naturally-occurring isomers of 3,4-dihydroxyproline is reported. L-2,3-cis-3,4-trans-3,4-Dihydroxyproline was synthesized from L-arabinose in 10 steps and 31% overall yield. The same series of reactions was employed to convert L-xylos

Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)

cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbamates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent α- and β-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield.

Facile synthesis of 3,4-dihydroxyprolines as an application of the L- threonine aldolase-catalyzed aldol reaction

A new facile synthesis of 3,4-dihydroxyprolines was attained by taking advantage of the L-threonine aldolase, which catalyzes the aldol condensation reaction of aldehydes with glycine affording β-hydroxy-α-L-amino acids.

A novel method for deprotection of N-9-phenylfluoren-9-yl group using iodine catalyst: Simple synthesis of (2S, 3R, 4R)-3,4-dihydroxyproline

Iodine was found to be an efficient catalyst for the deprotection of the N-phenylfluoren-9-yl (Pf) group in tertiary amine and promote an intramolecular amination. A facile and economical synthesis of (2S,3R,4R)- 3,4-dihydroxyproline was accomplished via iodine promoted cyclization and deprotection.

Efficient synthesis of a new aminoazasugar and dihydroxyprolines from an endocyclic enecarbamate

A novel procedure for the synthesis of trans-2,3-(2-aminomethyl)-cis-3,4-dihydroxypyrrolidine (a new aminoazasugar) and cis-2,3- and trans-2,3-cis-3,4-dihydroxyprolines is presented. Starting from the known endocyclic enecarbamate 1-carbobenzyloxy-2-pyrro

(±)-4-amino-4,5-dideoxyribose, (±)-4-amino-4-deoxyerythrose, and (±)-dihydroxyproline derivatives from N-dienyl-γ-lactams

Hetero-Diels-Alder cycloaddition of acylnitroso dienophile 4 with the N-(butadienyl)pyrrolidinone derivatives 2a,b led with complete regioselectivity to the oxazine adducts 5a,b. Sequential osmylation, protection of the ensuing glycol, and reduction of th

DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES FOR THE SYNTHESIS OF POLYHYDROXYPYRROLIDINES AS POTENTIAL ENZYMATIC INHIBITORS

Tosyl and benzyl azomethine ylides generated from the corresponding aziridines under thermal and photochemical conditions, were trapped by dipolar cycloaddition reaction with vinylene carbonate.The methoxycarbonyl group in the pyrrolidines obtained was re

Synthesis of (2S, 3R, 4R)-3,4-Dihydroxyproline from 2,5-Dibromo-2,5-dideoxy-D-xylono- or -lyxono-1,4-lactone

(2S, 3R, 4R)-3,4-dihydroxyproline (8) has been prepared in three steps from 2,5-dibromo-2,5-dideoxy-D-xylono-1,4-lactone (1).Azidolysis of 1 gave the 2-azido-5-bromo-2,5-dideoxy-D-lyxono-1,4-lactone (2), which by hydrogenolysis and hydrolysis gave 8.Azidolysis of 2,5-dibromo-2,5-dideoxy-D-lyxono-1,4-lactone (9) and 2,3-anhydro-5-bromo-5-deoxy-D-lyxono-1,4-lactone (10) also gave 2.Azidolysis of 10 in the absence of a proton donor led to degradation with evolution of nitrogen.

Synthesis of (3S,4S)-3,4-dihydroxyprolines from L-tartaric acid

Natural (2S,3S,4S)-3,4-dihydroxyproline (1) and the new (2R,3S,4S)-isomer (7) have been synthesized from L-tartaric acid via cyanosilylation of the cyclic Schiff base.