105990-40-7

Usage

Uses

Used in Medicinal Chemistry:
(2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol is utilized as a chiral building block for the synthesis of various pharmaceuticals. Its unique stereochemistry allows it to be a key component in the development of enantiomerically pure drugs, which is essential for ensuring the desired biological activity and minimizing side effects.
Used in Drug Development:
In the pharmaceutical industry, (2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol serves as a precursor in the creation of new drug candidates. Its potential biological activities and structural features make it a valuable compound for exploring novel therapeutic agents, particularly those targeting specific receptors or enzymes.
Used in Organic Synthesis:
(2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol is also used as an intermediate in organic synthesis. Its functional groups and chiral centers make it a versatile component for constructing complex organic molecules, which can be applied in various chemical and industrial processes.

Upstream product

• 100806-55-1 (2S,3S,4S)-2-benzyloxymethyl-3,4-dibenzyloxy-pyrrolidin 
• 57972-96-0 (E)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-bromo-acrylic acid ethyl ester 
• 115889-54-8 (2S,3S,4S)-4-Amino-2,3,5-trihydroxy-pentanal 
• 100806-54-0 1-azido-1-deoxy-4-O-methanesulphonyl-2,3,5-tri-O-benzyl-D-xylitol 
• 1579996-64-7 ((2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)pyrrolidin-2-yl)methanol 
• 105888-78-6 (3aS,4R,6aR)-4-Formyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 186025-85-4 (2S,3S)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester 
• 186025-75-2 (R)-(-)-methyl (Z)-3-(4,5-dihydro-2-phenyl-4-oxazolyl)-2-propenoate 
• 570385-37-4 (3aS,4S,6aR)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole 
• 570385-40-9 (S)-1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethane-1,2-diol 
• 570385-42-1 (3aS,4R,6aR)-2,2-Dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbaldehyde 
• 7306-64-1 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone 
• 649745-80-2 (S)-4-((4S,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 160797-20-6 (4S)-[(1S,2R)-dihydroxybut-3-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 100991-91-1 1,4-dideoxy-1,4-imino-L-arabinitol hydrochloride 
• 1333523-86-6 (2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-([2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy]methyl)pyrrolidine 
• 1333524-01-8 (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine 
• 1333523-84-4 (2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine 
• 1333523-99-1 (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine 
• 117894-12-9 (2S,3S,4S)-3,4-dihydroxy-2-hydroxymethyl-1-methylpyrrolidine 

Relevant academic research and scientific papers

Indium-mediated coupling of 3-bromopropenyl acetate with (S)-Garner aldehyde: a route to 1,4-dideoxy-1,4-L-iminoribitol

The indium organometallic complex generated by metallic indium and 3-bromopropenyl acetate in THF adds to the Garner aldehyde in excellent yield and with high diastereoselectivity; the usefulness of the corresponding anti-anti adduct was demonstrated by developing a short synthesis of the title compound, an azasugar known as a glycosidase inhibitor.

SYNTHESIS FROM D-MANNOSE OF 1,4-DIDEOXY-1,4-IMINO-L-RIBITOL AND OF THE α-MANNOSIDASE INHIBITOR 1,4-DIDEOXY-1,4-IMINO-D-TALITOL

The syntheses of 1,4-dideoxy-1,4-imino-L-ribitol and of 1,4-dideoxy-1,4-imino-D-talitol from D-mannose are described. 1,4-Dideoxy-1,4-imino-D-talitol is a specific and competitive inhibitor of human liver α-mannosidase in vitro and also blocks the lysosomal catabolism of asparigine-linked glycans of glycoproteins in vivo.

METHODS OF TREATING POMPE DISEASE

Disclosed herein are novel uses of ADMDP stereoisomers or their derivatives for the manufacture of a medicament for treating Pompe disease. Accordingly, the present disclosure provides a method of treating Pompe disease in a subject. The method includes the step of, administering to the subject a therapeutically effective amount of a compound of formula (I), or a salt, an ester or a solvate thereof, wherein R1 and R2 are independently H or alkyl optionally substituted by -NH2 or -OH, so as to ameliorate, alleviate mitigate and/or prevent symptoms associated with the Pompe disease. According to certain embodiments of the present disclosure, the compound of formula (I) may serve a stabilizer of α-glucosidase via preventing its denaturalization of deactivation.

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.

Synthesis of pyrrolidine iminosugars, (-)-lentiginosine, (-)-swainsonine and their 8a-epimers from d-glycals

Synthesis of pyrrolidine iminosugars has been described from d-glycals via dihydroxylation, oxidative cleavage and double nucleophilic displacement as the key steps. The pyrrolidines obtained have been utilized for the synthesis of important bicyclic iminosugars, viz. (-)-lentiginosine and (-)-swainsonine and their 8a-epimers, which are known to be glycosidase inhibitors.

An efficient synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol and 1,4-dideoxy-1,4-imino-d- and l-xylitol from chiral aziridines

A highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol (d-AB1, 1 and l-AB1, 3) and 1,4-dideoxy-1,4-imino-d- and l-xylitol (d-DIX, 2 and l-DIX, 4) starting from commercially available chiral aziridines was developed. The g

Redesign of the phosphate binding site of L -rhamnulose- 1-phosphate aldolase towards a dihydroxyacetone dependent aldolase

The aldol addition of unphosphorylated dihydroxyacetone (DHA) to aldehydes catalyzed by L-rhamnulose-1-phosphate aldolase (RhuA), a dihydroxyacetone phosphate-dependent aldolase, is reported. Moreover, a single point mutation in the phosphate binding site

A concise synthesis of (2 S,3 S,4 S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (LAB1)

The synthesis of (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (LAB1) from Garners aldehyde is described using the Sharpless asymmetric dihydroxylation as the key step. Georg Thieme Verlag Stuttgart - New York.

A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide

A highly diastereoselective synthesis of enantio-enriched all trans-3,4-dibenzyloxyl-5-benzyloxymethyl-2-pyrrolidinone 13a was developed based on SmI2-mediated benzyloxymethylation of O,O′-dibenzyltartarimide. The versatility of 13a and its antipode as the key building blocks for the asymmetric synthesis of pyrrolidine azasugars and homoazasugars has been demonstrated by elaborating them into naturally occurring DAB 1 (1), LAB 1 (2), N-hydroxyethyl-DAB 1 (4), 6-deoxy-DMDP 7, and 5-epi-radicamine B 36 as well as the reductive ring-opening product 35.

Borate as a phosphate ester mimic in aldolase-catalyzed reactions: Practical synthesis of L-fructose and L-iminocyclitols

Dihydroxyacetone phosphate (DHAP)-dependent aldolases have been widely used for the organic synthesis of unnatural sugars or derivatives. The practicality of using DHAP-dependent aldolases is limited by their strict substrate specificity and the high cost and instability of DHAP. Here we report that the DHAP-dependent aldolase L-rhamnulose 1-phosphate aldolase (RhaD) accepts dihydroxyacetone (DHA) as a donor substrate in the presence of borate buffer, presumably by reversible in situ formation of DHA borate ester. The reaction appears to be irreversible, with the products thermodynamically trapped as borate complexes. We have applied this discovery to develop a practical one-step synthesis of the non-caloric sweetener L-fructose. L-Fructose was synthesized from racemic glyceraldehyde and DHA in the presence of RhaD and borate in 92% yield on a gram scale. We also synthesized a series of L-iminocyclitols, which are potential glycosidase inhibitors, in only two steps.