59920-31-9

Basic information

• Product Name: 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL
• Synonyms: 2R,5R-BIS(HYDROXYMETHYL)-3R,4R-DIHYDROXYPYRROLIDINE;2,5-DIDEOXY-2,5-IMINO-D-MANNITOL;DMDP;2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine;(2R,5R)-bis(hydorxymethyl)-(3R,4R)-*dihydroxypyrr;(2R,5R)-BIS(HYDORXYMETHYL)-(3R,4R)-*DIHY DROXYPYRROL;2,5-Pyrrolidinedimethanol, 3,4-dihydroxy-, (2R,3R,4R,5R)-;DMDP[(2R,5R)-BIS(HYDROXYMETHYL)-(3R,4R)-DIHYDROXYPYRROLIDINE]
• CAS NO: 59920-31-9
• Molecular Formula: C₆H₁₃NO₄
• Molecular Weight: 163.17
• EINECS: 232-889-8
• Product Categories: Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;All Inhibitors;Glycosidase Inhibitors;Inhibitors;Carbohydrates & Derivatives
• Mol File: 59920-31-9.mol
• Article Data: 26

Chemical Properties

• Melting Point: 101-103°C
• Boiling Point: 395.9 °C at 760 mmHg
• Flash Point: 221.9 °C
• Appearance: Off-White Solid
• Density: 1.408 g/cm³
• Vapor Pressure: 6.55E-08mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL(59920-31-9)
• EPA Substance Registry System: 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL(59920-31-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 59920-31-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 59920-31-9 differently. You can refer to the following data:
1. A glucosidase inhibitor
2. A glucosidase inhibitor.

InChI:InChI=1/C6H13NO4/c8-1-3-5(10)6(11)4(2-9)7-3/h3-11H,1-2H2/t3-,4-,5-,6-/m1/s1

Upstream product

• 94801-02-2 5-azido-5-deoxy-D-fructopyranose 
• 934479-80-8 methanesulfonic acid 2,3,5-tris-benzyloxy-1-(1,2-dihydroxy-ethyl)-4-methanesulfonyloxy-pentyl ester 
• 934479-78-4 methanesulfonic acid 2,3-bis-benzyloxy-1-benzyloxymethyl-4-methanesulfonyloxy-hex-5-enyl ester 
• 474799-78-5 N-benzyl-3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-imino-D-mannitol 
• 176300-12-2 N-benzyl-3,4-di-O-benzyl-2,5-dideoxy-2,5-imino-D-mannitol 
• 165560-17-8 (2R,3R,4R,5R)-N-tert-butoxycarbonyl-3,4-bis(methoxymethyloxy)-5-hydroxymethyl-2-trityloxymethylpyrrolidine 
• 161290-43-3 (2R,3R,4R,5R)-2-(hydroxy-methyl)-3,4-di-O-benzyl-5-(O-benzyl-methyl)-pyrrolidine 
• 161867-56-7 Methanesulfonic acid (R)-1-[(4S,5R)-5-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester 
• 94801-02-2 5-azido-5-deoxy-D-fructopyranose 
• 98260-71-0 N-benzyloxycarbonyl-3-O-benzyyl-2,5-dideoxy-2,5-imino-D-mannitol 
• 132198-33-5 N-Benzhydryl-2,5-anhydro-2,5-imino-D-mannitol 
• 210115-92-7 (2R,3R,4R,5R)-2,5-bis(hydroxymethyl)-3,4-dihydroxypyrrolidine hydrochloride 
• 16054-77-6 3,5-di-O-benzyl-L-xylofuranose 
• 120693-81-4 (3aS,5S,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)dimethyl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxole 

Downstream Products

• 697288-31-6 (2R,3R,4R,5R)-N-(β-D-glucopyranosyl)thiocarbamoyl-3,4-dihydroxy-2,5-di(hydroxymethyl)-pyrrolidine 
• 697288-30-5 (2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(hydroxymethyl)-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamoylpyrrolidine 
• 697288-29-2 (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide 
• 697288-34-9 (5R,6R,7R,7aR)-6,7-Dihydroxy-5-hydroxymethyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 
• 697288-36-1 (5R,6R,7R,7aR)-6,7-Dihydroxy-5-hydroxymethyl-tetrahydro-pyrrolo[1,2-c]oxazole-3-thione 

Relevant articles and documents

Iminosugars from Baphia nitida Lodd.

Chromatographic separation of the 50% aqueous EtOH extract of the leaves of the African medicinal tree Baphia nitida resulted in isolation of 10 iminosugars. The plant contained 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (DMDP) as a major alkaloid. The structure of a new alkaloid was also elucidated by spectroscopic methods as the 1-O-β-d-fructofuranoside of DMDP, and this plant produced 3-O-β-d-glucopyranosyl-DMDP as well. DMDP is a potent inhibitor of β-glucosidase and β-galactosidase, whereas the other two derivatives lowered inhibition toward both of these enzymes and improved inhibitory activities toward rice α-glucosidase and rat intestinal maltase.

1,3-Oxazine as a chiral building block used in the total synthesis of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine

Concise and stereocontrolled syntheses of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine [(+)-DMDP] were achieved via a diastereomerically enriched oxazine intermediate. The key strategies include the use of 1,3-oxazine as a chiral building block and diastereoselective nucleophilic addition to an aldehyde. Starting from readily available (R)-methyl 2-benzamido-3-((tert-butyldimethylsilyl)oxy)propanoate, (+)-1-deoxynojirimycin was synthesized in 11 steps and 26.2% overall yield while (+)-DMDP was synthesized in 11 steps and 27.1% overall yield, respectively.

C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB- l -isoDMDP compared to miglitol and miglustat

The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. l-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 45% from d-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [Ki 0.081 μM for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by l-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis.