73111-27-0

Upstream product

• 73111-58-7 2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose 
• 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 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 260415-86-9 (3aR,4R,5S,6S)-4,5,6-tris(benzyloxy)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole 
• 219586-93-3 2,3,4-Tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose oxime 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 73111-12-3 methyl tri-O-benzyl-6-bromo-β-D-6-deoxy-glucopyranoside 

Downstream Products

• 73111-39-4 ((1R)-2t,3c,4t-tris-benzyloxy-5c-hydroxymethyl-cyclopentyl)-carbamic acid phenyl ester 
• 73135-46-3 (4aR)-5c,6t,7c-tris-benzyloxy-(4ar,7ac)-hexahydro-cyclopenta[d][1,3]oxazine-1-carboxylic acid phenyl ester 
• 73111-38-3 (4aR)-5c,6t,7c-tris-benzyloxy-(4ar,7ac)-hexahydro-cyclopenta[d][1,3]oxazin-2-one 
• 73111-42-9 (4aR)-5c,6t,7c-tris-benzyloxy-1-methyl-(4ar,7ac)-hexahydro-cyclopenta[d][1,3]oxazine 
• 73111-34-9 (3aR)-4c,5t,6c-trihydroxy-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole-1-carboxylic acid phenyl ester 
• 73111-33-8 (3aR)-4c,5t,6c-tris-benzyloxy-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole-1-carboxylic acid phenyl ester 
• 73111-37-2 ((1R)-2c-amino-3t,4c,5t-tris-benzyloxy-cyclopentyl)-methanol 

Relevant academic research and scientific papers

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.

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.

Stereocontrolled synthesis of polyhydroxylated hexahydro-1H-cyclopent[c]isoxazoles by intramolecular oxime olefin cycloadditions: An approach to aminocyclopentitols

A series of alk-5-enyl aldehydes derived from various carbohydrates (D-glucose, D-mannose, D-galactose, D-glucal) can be transformed into the corresponding oximes. Thermolysis of these oximes results in the isolation of hexahydro-1H-cyclopent[c]isoxazoles in good yields via intramolecular oxime olefin cycloadditions. Modest to excellent levels of diastereocontrol are observed in these cycloaddition reactions depending on the precise nature of the oxime precursor. In the best case, D-glucose-derived oxime 4 produces hexahydro-1H-cyclopent[c]isoxazole 5 as the sole product in quantitative yield. When the oxime possesses a substituent (OBn or OBz) adjacent to the oxime carbon atom, it is observed that reactions show a preference to produce the diastereomeric cycloadduct in which this substituent is located in an exo orientation relative to the newly formed hexahydro-1H-cyclopent[c]isoxazole ring system. The role of the solvent polarity on the diastereochemical outcome of these reactions is briefly discussed. Unsuccessful efforts to extend this chemistry to oximes derived from alk-4-enyl aldehydes are also presented. Finally, it is demonstrated that the hexahydro-1H-cyclopent[c]isoxazoles can be transformed into stereochemically defined aminocyclopentitols. The Royal Society of Chemistry 1999.

Stereoselective intramolecular oxime olefin cycloadditions involving carbohydrate derived precursors

Intramolecular oxime olefin cycloaddition reactions of carbohydrate derived precursors can be used to prepare highly functionalised 3-oxa-2-azabicyclo[3.3.0]hexanes with good to excellent levels of stereocontrol.