187339-50-0

Basic information

• Product Name: 1,4-dideoxy-1,4-imino-D-arabinitol
• Synonyms: (2R,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol; 1,4-Dideoxy-1,4-Imino-D-Mannitol
• CAS NO: 187339-50-0
• Molecular Formula: C₅H₁₁NO₃
• Molecular Weight: 133.1457
• Mol File: 187339-50-0.mol
• Article Data: 77

Chemical Properties

• Boiling Point: 319.1°C at 760 mmHg
• Flash Point: 188.8°C
• Density: 1.368g/cm³
• Vapor Pressure: 2.84E-05mmHg at 25°C
• Refractive Index: 1.554
• 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(187339-50-0)
• EPA Substance Registry System: 1,4-dideoxy-1,4-imino-D-arabinitol(187339-50-0)

Safety Data

• Hazardous Substances Data: 187339-50-0(Hazardous Substances Data)

Upstream product

• 734501-73-6 (3R,4S,5R)-5-Amino-tetrahydro-pyran-2,3,4-triol 
• 1101174-58-6 (6S,7S,7aR)-6,7-dihydroxy-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 
• 100806-49-3 (3aS,4R,6aR)-4-hydroxymethyl-2,2-dimethyl-tetrahydro-1,3-dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 1105054-49-6 (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide 
• 186025-88-7 Benzoic acid (2S,3R,4R)-3,4-dihydroxy-5-oxo-pyrrolidin-2-ylmethyl 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 
• 108692-47-3 (2R,3R,4R)-2-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol 
• 105878-97-5 (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol 
• 135395-48-1 (3R,4R)-5-Hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol 
• 211995-45-8 Benzoic acid (2R,3R,4S)-3,4-dihydroxy-5-oxo-pyrrolidin-2-ylmethyl ester 
• 214619-39-3 Methanesulfonic acid (4R,5R)-5-[(R)-2-hydroxy-1-(9-phenyl-9H-fluoren-9-ylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 67561-03-9 N-benzyloxycarbonylglycinal 

Downstream Products

• 117894-12-9 (2S,3S,4S)-3,4-dihydroxy-2-hydroxymethyl-1-methylpyrrolidine 
• 117894-12-9 1,4-dideoxy-1,4-(methyliminiumyl)-D-arabinitol 

Relevant articles and documents

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

A common strategy towards the synthesis of 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars

A strategy towards the synthesis of three different target molecules, namely 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars, molecules of potential biological and medicinal significance, is reported from a common amino-vicinal diol intermediate derived from tri-O-benzyl-D-glucal. Construction of the key pyrrolidine ring present in 1,4-dideoxy-1,4-imino-L-xylitol and (+)-anisomycin was a consequence of thermodynamically driven concomitant intramolecular nucleophilic addition reaction of the amino group to the resultant aldehyde obtained by oxidative cleavage of the amino-vicinal diol. Alternatively, double nucleophilic substitution on an amino-diol, after mesylation, with various amines delivered amino-substituted piperidine iminosugars in good yields.

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