105015-44-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S,5S)-Bishydroxymethyl-(3R,4R)-bishydroxypyrrolidine is used as a potent and specific glycosidase inhibitor for its potential as an antiviral agent. Its ability to inhibit glycosidase enzymes can help in the development of new antiviral therapies and treatments.
Used in Biotechnology Industry:
(2S,5S)-Bishydroxymethyl-(3R,4R)-bishydroxypyrrolidine is used as a research tool for studying the role of glycosidase enzymes in various biological processes. Its specificity as an inhibitor can aid in understanding the mechanisms of these enzymes and their potential as targets for therapeutic intervention.

InChI:InChI=1/C6H13NO4/c8-1-3-5(10)6(11)4(2-9)7-3/h3-11H,1-2H2/t3-,4-,5+,6+/m0/s1

Upstream product

• 144397-81-9 (2S,3R,4R,5S)-1-Benzyl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol; hydrochloride 
• 132803-73-7 5-azido-5-deoxy-L-sorbose 
• 111275-74-2 1,3:4,6-di-O-benzyliidene-2,5-di-O-trifluoromethylsulphonyl-D-mannitol 
• 111248-46-5 N-amino-1,3:4,6-di-O-benzylidene-2,5-dideoxy-2,5-imino-L-iditol 
• 144266-28-4 2,5-dideoxy-2,5-N-benzylimino-1,3:4,6-di-O-benzylidene-L-iditol 
• 28224-74-0 1,3:4,6-di-O-benzylidene-2,5-di-O-methanesulfonyl-D-mannitol 
• 28224-73-9 1,3:4,6-di-O-benzylidene-D-mannitol 
• 176166-98-6 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-2,6-di-O-methanesulfonyl-L-gulitol 
• 157363-88-7 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-L-gulitol 
• 157363-85-4 1,2:5,6-Dianhydro-3,4-di-O-benzyl-D-mannitol 
• 36199-02-7 3,4-di-O-benzyl-D-mannitol 
• 872360-66-2 (2S,3R,4R,5S)-N-benzyl-2-hydroxymethyl-3,4-dibenzyloxy-5-[(benzyloxy)methyl]-pyrrolidine 
• 881185-77-9 (2S,3R,4R,5S)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)pyrrolidine 
• 176166-99-7 N-benzyl-3,4-di-O-benzyl-2,5-dideoxy-2,5-imino-L-iditol 

Relevant academic research and scientific papers

SYNTHESIS OF (2S,5S)-BISHYDROXYMETHYL-(3R,4R)-BISHYDROXYPYRROLIDINE FROM D-MANNITOL

A short, efficient, and practical synthesis of (2S,5S)-bishydroxymethyl-(3R,4R)-bishydroxypyrrolidine from D-mannitol involving five sequential reactions (benzylidenation, trifluoromethanesulphonation, hydrazinolysis, hydrogenolysis, and deacetalisation)

Synthesis of dihydroxymethyl dihydroxypyrrolidines and steviamine analogues from C-2 formyl glycals

Synthesis of dihydroxymethyl dihydroxypyrrolidines from C-2 formyl d-glycals has been described via a common dicarbonyl intermediate. The hence obtained pyrrolidines have been further utilized for the synthesis of some steviamine analogues. The newly synthesized molecules have been evaluated for glycosidase inhibition against 6 commercially available enzymes and found to be active in the micromolar range, where one of the steviamine analogues showed good and selective inhibition of β-mannosidase (Helix pomatia).

Concise synthesis of iminocyclitols via petasis-type aminocyclization

(Chemical Equation Presented) A two-step method has been developed to synthesize several biologically important iminocyclitols in ca. 44-60percent yields by using Petasis-type condensation. The method is very generaland operationally simple, affording a s

A glycal approach towards an efficient and stereodivergent synthesis of polyhydroxypyrrolidines

A stereo-defined synthesis of two diastereomers of polyhydroxypyrrolidines from 3,4,6-tri-O-benzyl-d-glucal 4 involving a cleavage-recyclization strategy is reported. Hemiacetal 7 obtained from glucal 4, upon reduction with LiAlH 4 afforded dio

Iminosugars as glycosyltransferase inhibitors: Synthesis of polyhydroxypyrrolidines and their evaluation on chitin synthase activity

Chitin synthase is an enzyme involved in the biosynthesis of chitin, a major structural component of the cell wall of many fungi. Since chitin is absent in vertebrates, chitin synthase has been envisaged as a valuable target in the search for new antifung

Chemoenzymatic preparation of novel cyclic imine sugars and rapid biological activity evaluation using electrospray mass spectrometry and kinetic analysis

Cyclic imine sugars were prepared by a novel chemoenzymatic strategy in which azido-sugars, constructed by enzymatic aldol reactions, were hydrogenated under acidic conditions. These cyclic imine sugars were found to be potent inhibitors of glycoprocessing enzymes having K(i)'s in the nanomolar and micromolar range for a variety of glycosidases. In comparison with their fully hydrogenated counterparts the cyclic imine sugars generally showed comparable or better inhibition against the glycosidases tested. Because these cyclic imines are so readily available and since imines are key intermediates in a variety of cycloadditions, condensations, and nucleophilic additions, they are valuable as versatile synthetic intermediates for the preparation of navel iminocyclitols and derivatives. An example of such synthetic utility is demonstrated by the synthesis of amino-iminocyclitol 24 via a three-center, two-component Strecker reaction. A novel method for rapidly screening glycosidase inhibitors using electrospray mass spectrometry is also described and shown to be capable of identifying potent fucosidase inhibitors for detailed kinetic analysis. Also, in the reductive amination of azido-sugars for the preparation of the five-membered ring iminocyclitol 8, rhodium was found to exhibit superior face selectivity when compared to palladium or platinum catalysts.

Synthesis of azasugars as potent inhibitors of glycosidases

A series of enantiomerically pure azasugars (2,5-dideoxy-2,5-imino-D-mannitol, 1-deoxynojirimycin, 1-deoxymannojirimycin, and related compounds) was synthesized from D-mannitol via aminoheterocyclization of C2-symmetric bis-epoxides and subsequently followed by ring isomerization in few cases. These compounds have been evaluated as inhibitors of several glycosidases (α- and β-D-glucosidases, α-D-mannosidase and α-L-fucosidase). Inhibition studies indicate notably that the polyhydroxylated azepanes are inhibitors of glycosidases, with K(i) in the micromolar range.

Synthesis of azasugars. Part 1. Isomerization of polyhydroxylated piperidines

N-Benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol and L-gulitol undergo easy isomerization, mainly either by ring contraction, or either by SN2 inversion at C2. This isomerization performed by bis-hydroxyl activation allows to access to 2,5-dideoxy-2,5-imino-L-iditol, 5-epi-DNJ, DMDP, and DMJ.

Short-step synthesis of chiral C2-symmetric 2,3,4,5-tetrasubstituted pyrrolidines from D-mannitol and their use as chiral ligands in the reaction of diethylzinc and benzaldehyde

(3R,4R)-bis(hydroxy)-(2S,5S)-bis(hydroxymethyl)-pyrrolidine and related chiral C2-symmetric pyrrolidines including D2-symmetric 1,2-bis(1-pyrrolidino)-ethanes and N-hydroxyethylpyrrolidines were synthesized highly practically from D-