129568-47-4

Upstream product

• 129492-78-0 (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine 
• 186025-88-7 Benzoic acid (2S,3R,4R)-3,4-dihydroxy-5-oxo-pyrrolidin-2-ylmethyl ester 
• 274910-85-9 3,4-O-dimethoxymethyl-6-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-L-lyxitol 
• 18524-19-1 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol 
• 274910-78-0 1,2-anhydro-4,5-isopropylidene-3-methoxymethyl-D-ribitol 
• 274910-80-4 1-azido-4,5-O-isopropylidene-3-methoxymethyl-1-deoxy-D-ribitol 
• 274910-82-6 1-azido-2,3-O-dimethoxymethyl-1-deoxy-D-ribitol 
• 274910-81-5 1-azido-2,3-O-dimethoxymethyl-4,5-O-isopropylidene-1-deoxy-D-ribitol 
• 274910-83-7 1-azido-2,3-O-dimethoxymethyl-5-O-tert-butyldimethylsilyl-1-deoxy-D-ribitol 
• 274910-84-8 1-azido-2,3-O-dimethoxymethyl-4-O-methanesulfonyl-5-O-tert-butyldimethylsilyl-1-deoxy-D-ribitol 
• 186025-75-2 (R)-(-)-methyl (Z)-3-(4,5-dihydro-2-phenyl-4-oxazolyl)-2-propenoate 
• 186025-84-3 (2R,3R)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester 
• 1101174-62-2 (6S,7R,7aS)-6,7-dihydroxy-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 
• 40773-81-7 ((2S,3S,4R)-2,3,4,5-Tetrahydroxy-pentyl)-carbamic acid benzyl 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

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.

Anin vitro-in vivosequential cascade for the synthesis of iminosugars from aldoses

Here, we report a chemoenzymatic approach for the preparation of a small panel of biologically important iminosugars from readily available aldoses. Our approach involves anin vitrotransaminase-mediated amination of aldoses in combination with anin vivose

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.

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.

Total synthesis without protecting groups: Pyrrolidines and cyclic carbamates

(Chemical Equation Presented) A protecting group free synthesis of 2,3-cis substituted hydroxypyrrolidines is reported. Two novel reaction methodologies allow for the stereoselective formation of cyclic carbamates from olefinic amines, and the formation o

Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit na

Benzhydryl protection by diphenyldiazomethane of an alcohol in enantiomeric base-sensitive ribonolactones allows short efficient syntheses of 1,4-dideoxy-1,4-imino-d-lyxitol (DIL) and of 1,4-dideoxy-1,4-imino-l-lyxitol (LIL). DIL showed potent [Ki/s

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.