1354826-63-3

Upstream product

• 1354826-56-4 (3R,4R,5R,6S,7S) 7-allyl-4,5,6-tris(benzyloxy)azepan-3-ol 
• 100-39-0 benzyl bromide 
• 223912-28-5 allyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-β-D-glucopyranoside 
• 1357297-00-7 allyl 6-azido-6-deoxy-β-D-glucopyranoside 
• 223912-26-3 allyl 6-(4-methylbenzenesulfonate)-β-D-glucopyranoside 
• 10343-15-4 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 
• 604-69-3 β-D-glucose pentaacetate 
• 19139-89-0 (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 
• 114219-26-0 methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 1354826-73-5 (2S,3S,4R,5S,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-fluoroazepane 
• 1354826-71-3 (2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine 
• 1354826-75-7 (2S,3S,4R,5R,6R)-2-allyl-6-azido-1-benzyl-3,4,5-tris(benzyloxy)azepane 
• 1354826-74-6 (2S,3S,4R,5R,6S)-2-allyl-6-(azidomethyl)-1-benzyl-3,4,5-tris(benzyloxy)piperidine 
• 1354826-65-5 (2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(chloromethyl)piperidine 
• 1449009-42-0 ((2S,3R,4R,5S,6S)-6-allyl-1-benzyl-3,4,5-tris(benzyloxy)piperidin-2-yl)methanol 
• 860264-32-0 (2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine 

Relevant academic research and scientific papers

Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog

A new family of chiral C2 symmetric tetraazamacrocycles, coined ISAC for IminoSugar Aza-Crown, incorporating two iminosugars adopting a 4C1 conformation is disclosed. Multinuclear NMR experiments on the corresponding Cdsu

Skeletal rearrangement of seven-membered iminosugars: Synthesis of (-)-adenophorine, (-)-1-epi-adenophorine and derivatives and evaluation as glycosidase inhibitors

The mirror image of natural product (+)-adenophorine along with its 1-epi-, 1-homo-analogs and other derivatives have been synthesized and evaluated as glycosidase inhibitors. The synthetic strategy is based on the skeletal rearrangement of tetrahydroxylated C-alkyl azepanes obtained via a Staudinger/azaWittig/alkylation sequence starting from a sugar-derived azidolactol. Several organometallic species have been investigated for the alkylation step including organomagnesium, organolithium, organozinc, organoaluminum and organocerium reagents. While diallylzinc proved to be the most efficient to introduce an allyl substituent, disappointing results were obtained with the other organometallic species leading either to lower yields or no reaction. Enzymatic assays indicate that (-)-adenophorine is a moderate α-l-fucosidase inhibitor.

Access to L-and D-iminosugar C-glycosides from a D-gluco-derived 6-azidolactol exploiting a ring isomerization/alkylation strategy

A flexible synthetic access to six-membered l- and d-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3, 4-tri-O-benzyl-d-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.