100937-52-8

Basic information

• Product Name: 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL
• Synonyms: 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL;2-HYDROXYMETHYL-3,4-PYRROLIDINEDIOL;1,4-Dideoxy-1,4-imino-D-mannitol;(2R)-2α-(Hydroxymethyl)pyrrolidine-3β,4α-diol;(2R)-3β,4α-Dihydroxy-2α-pyrrolidinemethanol;(2R)-3β,4α-Dihydroxypyrrolidine-2-methanol;(2R)-3β,4α-Dihydroxypyrrolidine-2α-methanol;1,4-Imino-1,4-dideoxy-D-arabinitol
• CAS NO: 100937-52-8
• Molecular Formula: C₅H₁₁NO₃
• Molecular Weight: 133.15
• Product Categories: Miscellaneous Natural Products
• Mol File: 100937-52-8.mol

Chemical Properties

• Melting Point: 113 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))
• Boiling Point: 319.1°C at 760 mmHg
• Flash Point: 188.8°C
• Appearance: /
• Density: 1.368g/cm³
• Vapor Pressure: 2.84E-05mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: 2-8°C
• PKA: 14.13±0.60(Predicted)
• CAS DataBase Reference: 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL(100937-52-8)
• EPA Substance Registry System: 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL(100937-52-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 100937-52-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H11NO3/c7-2-3-5(9)4(8)1-6-3/h3-9H,1-2H2/t3-,4-,5-/m1/s1

Upstream product

• 105878-97-5 (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol 
• 191723-91-8 (2R,3R)-N-(4-methoxybenzyl)-2,3-dihydroxy-4-cyanopyrrolidine 
• 191723-92-9 (2R,3R)-N-(4-methoxybenzyl)-2,3-dihydroxy-4-cyanopyrrolidine 
• 139877-36-4 (3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-one 
• 34370-91-7 3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 131053-14-0 3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-xylo-furanose 
• 100991-92-2 (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine hydrochloride 
• 537030-19-6 (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide 
• 1029529-50-7 (R,E)-N-(1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl)benzamide 
• 1029529-52-9 N-((2R,3S,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide 
• 1349697-11-5 (4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine 
• 1349697-02-4 (3R,4R,5R)-4-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-3-yl benzoate 
• 1349697-05-7 N-((5S,6R)-5-((E)-3-chloroprop-1-enyl)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-yl)benzamide 
• 245484-08-6 (2S,3S,4S)-2-Hydroxymethyl-1-(4-methoxy-benzyl)-pyrrolidine-3,4-diol 

Downstream Products

• 117894-12-9 1,4-dideoxy-1,4-(methyliminiumyl)-D-arabinitol 
• 100991-91-1 1,4-dideoxy-1,4-imino-L-arabinitol hydrochloride 
• 117894-12-9 (2S,3S,4S)-3,4-dihydroxy-2-hydroxymethyl-1-methylpyrrolidine 
• 1333523-99-1 (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-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 
• 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 
• 1333523-86-6 (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 
• 117383-70-7 2,3-di-O-benzoyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-5-O-triphenylmethyl-D-arabinitol 
• 117383-69-4 N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-5-O-triphenylmethyl-D-arabinitol 
• 117383-71-8 2,3-di-O-benzoyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol 
• 117383-68-3 2,3,5-tri-O-acetyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol 
• 117383-72-9 2,3-di-O-benzoyl-1,4-dideoxy-1,4-imino-D-arabinitol 
• 105878-97-5 (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol 

Relevant articles and documents

Iminosugars as potential inhibitors of glycogenolysis: Structural insights into the molecular basis of glycogen phosphorylase inhibition

Iminosugars DAB (5), isofagomine (9), and several N-substituted derivatives have been identified as potent inhibitors of liver glycogen phosphorylase a (IC50 = 0.4-1.2 μM) and of basal and glucagon-stimulated glycogenolysis (IC50 = 1-3 μM). The X-ray structures of 5, 9, and its N-3-phenylpropyl analogue 8 in complex with rabbit muscle glycogen phosphorylase (GPb) shows that iminosugars bind tightly at the catalytic site in the presence of the substrate phosphate and induce conformational changes that characterize the R-state conformation of the enzyme. Charged nitrogen N1 is within hydrogen-bonding distance with the carbonyl oxygen of His377 (5) and in ionic contact with the substrate phosphate oxygen (8 and 9). Our findings suggest that the inhibitors function as oxocarbenium ion transition-state analogues. The conformational change to the R state provides an explanation for previous findings that 5, unlike inhibitors that favor the T state, promotes phosphorylation of GPb in hepatocytes with sequential inactivation of glycogen synthase.

Use of a recombinant bacterial fructose-1,6-diphosphate aldolase in aldol reactions: Preparative syntheses of 1-deoxynojirimycin, 1-deoxymannojirimycin, 1,4-dideoxy-1,4-imuno-D-arabinitol, and fagomine

A combined enzymatic aldol condensation and catalytic intramolecular reductive amination has been used in the high-yield asymmetric synthesis of polyhydroxylated alkaloids including 1-deoxynojirimycin, 1-deoxymannojirimycin, 1,4-dideoxy-1,4-imino-D-arabinitol, and fagomine. The Escherichia coli Zn2+-containing fructose-1,6-diphosphate aldolase overexpressed in E. coli was used for the syntheses. The enzyme in aqueous solution containing 0.3 mM ZnCl2 has excellent stability with a half-life of 60 days, compared to 2 days for the enzyme from rabbit muscle. The reactions were carried out under mild conditions without protection of functional groups. Either dihydroxyacetone phosphate or a mixture of dihydroxyacetone and inorganic arsenate can be used as donor in the aldol reactions. The aldol acceptors (R)- and (S)-3-azido-2-hydroxypropanal were prepared via lipase-catalyzed resolution of the racemic acetal precursor.

Synthesis of hydroxylated pyrrolidines by allenic cyclisation

The diastereoselective gold(I) catalysed cyclisation of highly substituted aminoallene derivatives allows the synthesis of both epi-DAB-1 and di-epi-lentiginosine. While the sense of stereoselectivity observed is in line with earlier observations on analo

A short diastereoselective synthesis of the natural (2R, 3R, 4R)-2-hydroxymethyl-3,4-dihydroxypyrrolidine

1,4-Dideoxy-1,4-imino-D-arabinitol 1, a glycosidase inhibitor constituent of Arachniodes standishii 1 and angylocalyx boutiqueanus2 was synthesized from (S)-pyroglutamic acid through regioselective ring opening of the epoxide 3.

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

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.

Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB

A diastereoselective concise synthesis of the iminosugars DMDP and DAB is presented starting from l-xylose and affording the two alkaloids in good yields of 35% and 22% over seven and eight steps, respectively. The Petasis borono-Mannich reaction of 3,5-di-O-benzyl-l-xylofuranose with benzylamine and (E)-styrylboronic acid served as the nitrogen-introducing key step furnishing the new C-N bond in an entirely diastereoselective manner. A chemo- and regioselective O-mesylation followed by an intramolecular SN2- cyclisation allowed the formation of the pyrrolidine ring. Ozonolysis of the styryl double bond and subsequent reduction to form the C-5 hydroxymethyl substituent followed by hydrogenolysis of the benzyl protecting groups concluded the DMDP synthesis. Furthermore, an unexpected fragmentation process during the ozonolysis reaction also gave access to the C-5 decarbinolated DMDP derivative DAB.

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