73111-37-2

Basic information

• Product Name: ((1R)-2c-amino-3t,4c,5t-tris-benzyloxy-cyclopentyl)-methanol
• Synonyms: ((1R)-2c-amino-3t,4c,5t-tris-benzyloxy-cyclopentyl)-methanol
• CAS NO: 73111-37-2
• Molecular Weight: 433.547
• Mol File: 73111-37-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ((1R)-2c-amino-3t,4c,5t-tris-benzyloxy-cyclopentyl)-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: ((1R)-2c-amino-3t,4c,5t-tris-benzyloxy-cyclopentyl)-methanol(73111-37-2)
• EPA Substance Registry System: ((1R)-2c-amino-3t,4c,5t-tris-benzyloxy-cyclopentyl)-methanol(73111-37-2)

Safety Data

• Hazardous Substances Data: 73111-37-2(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 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 
• 73111-39-4 ((1R)-2t,3c,4t-tris-benzyloxy-5c-hydroxymethyl-cyclopentyl)-carbamic acid phenyl ester 
• 73111-43-0 1L-(1,2,4/3,5)-3,4,5-tri-O-benzyl-2-(dimethylamino)-1-(hydroxymethyl)cyclopentane-3,4,5-triol 
• 73111-42-9 (4aR)-5c,6t,7c-tris-benzyloxy-1-methyl-(4ar,7ac)-hexahydro-cyclopenta[d][1,3]oxazine 

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.