319924-32-8

Basic information

• Product Name: 1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol
• Synonyms: 1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol
• CAS NO: 319924-32-8
• Molecular Weight: 331.53
• Mol File: 319924-32-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol(319924-32-8)
• EPA Substance Registry System: 1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol(319924-32-8)

Safety Data

• Hazardous Substances Data: 319924-32-8(Hazardous Substances Data)

Upstream product

• 53215-95-5 N-(trimethylsilylmethyl)benzylamine 
• 319924-31-7 (4S,5R)-4-(Bromomethyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane 
• 319924-29-3 1,1-Dibromo-5-[(tert-butyldimethylsilyl)oxy]-1,2-dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-ene 
• 100-46-9 benzylamine 
• 319924-30-6 5-[(tert-Butyldimethylsilyl)oxy]-1,2-dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-yne 
• 320396-46-1 1,2-Dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-ynitol 
• 125993-65-9 (4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 

Downstream Products

• 169105-89-9 isofagomine 
• 215724-77-9 N-benzyl (+)-isofagomine 
• 319924-34-0 [(3aR,7R,7aR)-5-Benzyl-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]pyridin-7-yl]methanol 
• 319924-33-9 (3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine 

Relevant articles and documents

Synthesis of polyhydroxy piperidines and their analogues: A novel approach towards selective inhibitors of α-glucosidase

Various polyhydroxy piperidine azasugars have been synthesized from precursors 18a and 18b, obtained in both enantiomeric forms from d-ribose. Out of these polyhydroxy piperidine azasugars, 22, 39 and 20 were found to be potent as well as selective inhibitors of α-glucosidase with Ki values ranging as low as 1.07 μM, 16.4 μM, and 88.2 μM, respectively. Replacement of the hydroxy methylene moiety of 19 (Ki 33% at 1 mM) by an amino methylene moiety (32, Ki 36.8 μM) showed a remarkable increase in the activity (almost 30 times). Furthermore, increasing the lipophilicity of 33 by N-alkylation with a dodecyl group (36) showed a three-fold enhancement in the activity (Ki 217 μM to Ki 72.3 μM). The Royal Society of Chemistry 2008.

A general strategy towards the synthesis of 1-N-iminosugar type glycosidase inhibitors: Demonstration by the synthesis of D- as well as L-glucose type iminosugars (isofagomines)

Both enantiomers of isofagomine, the potent glycosidase inhibitor of a type 1-N-iminosugar have been synthesized by the intramolecular cyclization of the PET generated α-trimethylsilylmethylamine radical cation with the appropriate tethered acetylene moiety. (C) 2000 Published by Elsevier Science Ltd.