219586-93-3

Basic information

• Product Name: 2,3,4-Tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose oxime
• Synonyms: 2,3,4-Tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose oxime
• CAS NO: 219586-93-3
• Molecular Weight: 431.532
• Mol File: 219586-93-3.mol

Chemical Properties

• CAS DataBase Reference: 2,3,4-Tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-Tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose oxime(219586-93-3)
• EPA Substance Registry System: 2,3,4-Tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose oxime(219586-93-3)

Safety Data

• Hazardous Substances Data: 219586-93-3(Hazardous Substances Data)

Upstream product

• 73111-58-7 2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 73111-37-2 ((1R)-2c-amino-3t,4c,5t-tris-benzyloxy-cyclopentyl)-methanol 
• 910033-61-3 N-((2S,3S,4R)-2,3,4-Tris-benzyloxy-hex-5-enyl)-hydroxylamine 
• 260415-86-9 (3aR,4R,5S,6S)-4,5,6-tris(benzyloxy)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole 
• 73111-27-0 (1R,5R,6R,7S,8S)-6,7,8-tri-O-benzyl-3-oxa-2-azabicyclo[3.3.0]octane-6,7,8-triol 

Relevant articles and documents

Structure–Activity Studies of N-Butyl-1-deoxynojirimycin (NB-DNJ) Analogues: Discovery of Potent and Selective Aminocyclopentitol Inhibitors of GBA1 and GBA2

Analogues of N-butyl-1-deoxynojirimycin (NB-DNJ) were prepared and assayed for inhibition of ceramide-specific glucosyltransferase (CGT), non-lysosomal β-glucosidase 2 (GBA2) and the lysosomal β-glucosidase 1 (GBA1). Compounds 5 a–6 f, which carry sterically demanding nitrogen substituents, and compound 13, devoid of the C3 and C5 hydroxy groups present in DNJ/NB-DGJ (N-butyldeoxygalactojirimycin) showed no inhibitory activity for CGT or GBA2. Inversion of stereochemistry at C4 of N-(n-butyl)- and N-(n-nonyl)-DGJ (compounds 24) also led to a loss of activity in these assays. The aminocyclopentitols N-(n-butyl)- (35 a), N-(n-nonyl)-4-amino-5-(hydroxymethyl)cyclopentane- (35 b), and N-(1-(pentyloxy)methyl)adamantan-1-yl)-1,2,3-triol (35 f), were found to be selective inhibitors of GBA1 and GBA2 that did not inhibit CGT (>1 mm), with the exception of 35 f, which inhibited CGT with an IC50 value of 1 mm. The N-butyl analogue 35 a was 100-fold selective for inhibiting GBA1 over GBA2 (Ki values of 32 nm and 3.3 μm for GBA1 and GBA2, respectively). The N-nonyl analogue 35 b displayed a Ki value of ?14 nm for GBA1 inhibition and a Ki of 43 nm for GBA2. The N-(1-(pentyloxy)methyl)adamantan-1-yl) derivative 35 f had Ki values of ≈16 and 14 nm for GBA1 and GBA2, respectively. The related N-bis-substituted aminocyclopentitols were found to be significantly less potent inhibitors than their mono-substituted analogues. The aminocyclopentitol scaffold should hold promise for further inhibitor development.

Intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α-d-glucopyranoside

The intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α-d-glucopyranoside with 2-furaldehyde has been studied. This cycloaddition was found to afford three 9-oxa-1-azabicyclo[4.2.1] nonane diastereomers in a 3:1:1 ratio

An intramolecular 1,3-dipolar cycloaddition reaction towards the synthesis of chiral azetidine nucleoside analogues: The D-gluco case

The diastereoselective intramolecular 1,3-dipolar cycloaddition reaction of unsaturated nitrones, derived from methyl α-D-glucopyranoside with 2-furaldehyde and 2-(benzyloxy)acetaldehyde has been studied. In our pevious studies with 2-furaldehyde, the cyc

Diastereocontrol in the intramolecular cycloadditions of 2- substituted-erythro-3,4-isopropylidenedioxyhex-5-enenitrile oxides

The influence of the 2-substituent on the diastereoselectivity of the intramolecular cycloadditions in a series of 2-substituted-erythro-3,4-isopropylidenedioxyhex-5- enenitrile oxides, generated in situ from selected sugar derivatives, was examined.