1129725-67-2

Upstream product

• 366815-78-3 (2S,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)piperidine 
• 160549-11-1 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 1600532-62-4 (2S,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-1-(furan-2-ylmethyl)piperidine 
• 911141-03-2 (3R,4R,5R)-3,4,6-tris(benzyloxy)hexane-1,5-diol 

Relevant academic research and scientific papers

Concise and highly stereoselective syntheses of D-fagomine and 2-epi-fagomine

Highly stereoselective total syntheses of polyhydroxylated piperidines D-fagomine and 2-epi-fagomine have been developed starting from 3,4,6-tri-O-benzyl-D-glucal which is a derivative of D-Glucose. Key steps in the synthesis of these azasugars involved N-Boc-protected amine preparation from oxime followed by stereo specific iodination of alcohol and cascade cyclization triggered by N-Boc deprotection.

Applications and limitations of the I2-mediated carbamate annulation for the synthesis of piperidines: Five-versus six-membered ring formation

A protecting-group-free synthetic strategy for the synthesis of piperidines has been explored. Key in the synthesis is an I2-mediated carbamate annulation, which allows for the cyclization of hydroxy-substituted alkenylamines into piperidines, pyrrolidines, and furans. In this work, four chiral scaffolds were compared and contrasted, and it was observed that with both d-galactose and 2-deoxy-d-galactose as starting materials, the transformations into the piperidines 1-deoxygalactonorjirimycin (DGJ) and 4-epi-fagomine, respectively, could be achieved in few steps and good overall yields. When d-glucose was used as a starting material, only the furan product was formed, whereas the use of 2-deoxy-d-glucose resulted in reduced chemo- and stereoselectivity and the formation of four products. A mechanistic explanation for the formation of each annulation product could be provided, which has improved our understanding of the scope and limitations of the carbamate annulation for piperidine synthesis.

Assessment of partially deoxygenated deoxynojirimycin derivatives as glucosylceramide synthase inhibitors

Glucosylceramide synthase (GCS) is an approved drug target for the treatment of Gaucher disease and is considered as a valid target for combating other human pathologies, including type 2 diabetes. The clinical drug N-butyldeoxynojirimycin (Zavesca) is thought to inhibit through mimicry of its substrate, ceramide. In this work we demonstrate that, in contrast to what is proposed in this model, the C2-hydroxyl of the deoxynojirimycin core is important for GCS inhibition. Here we show that C6-OH appears of less important, which may set guidelines for the development of GCS inhibitors that have less affinity (in comparison with Zavesca) for other glycoprocessing enzymes, in particular those hydrolases that act on glucosylceramide.

A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition

A novel and concise scheme has been developed successfully for the syntheses of N-substituted fagomine derivatives. The transformation of lactone (2) to 1,5-diol (3) was carried on with high yield (93-95%). The cyclization of 4 to 5 is a high stereoselect

Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors

We report the structure-activity relationship of a series of d-, and l-isofagomine and fagomine isomers as glycosidase inhibitors. Our study revealed that a positive charge at the anomeric position of d-isofagomines enhanced the potency toward β-glycosida

A synthesis of 2-epi-fagomine using gold(I)-catalysed allene cyclisation

A synthesis of 2-epi-fagomine via a highly stereoselective gold(I)-catalysed allene cyclisation is described. The stereochemical outcome of the cyclisation is opposite to that observed in previous studies. In contrast, gold(III)-catalysed cyclisation is i

Efficient and stereodivergent syntheses of D- and L-fagomines and their analogues

The syntheses of D- and L-fagomines 1, 4, 5 and 6 and their isomers from starting D-glycals have been achieved. The syntheses involve elaboration of common amino alcohol precursors obtained from 2-deoxy-1-amino sugar derivatives. The key steps in the synt