121435-63-0

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 151593-17-8 N-benzyl-2,3,5-tri-O-benzyl-D-arabinofuranosylamine 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 100-46-9 benzylamine 

Downstream Products

• 151508-02-0 (3S,4R,5S)-N-benzyl-3,4-dibenzyloxy-5-ethenylpyrrolidin-2-one 
• 151507-95-8 (2S,3R,4R,5S)-N-benzyl-3,4-dibenzyloxy-5-[(benzyloxy)methyl]-2-vinyl-pyrrolidine 
• 146579-10-4 4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-1,2,3-trideoxy-D-gluco-hept-1-enitol 
• 420846-49-7 2-O-acetyl-N-benzyl-4,5,7-tri-O-benzyl-1,3-dideoxy-1,3-imino-D-glycero-D-ido-heptitol 
• 151508-05-3 (2S,3R,4R)-3,4-Bis-benzyloxy-2-ethyl-pyrrolidine 

Relevant academic research and scientific papers

A New Procedure for the Synthesis of D-Glucosamine α-C-Glycosides

Reaction of (2,3,5-tri-O-benzyl-D-arabinofuranosyl)benzylamine with vinylmagnesium bromide and subsequent mercuriocyclisation of the obtained open-chain product, provides a stereoselective entry to α-C-glycosides of D-glucosamine.

Reinvestigation of the iodocyclization of 4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-1,2,3-trideoxy-D-gluco-hept-1- enitol: Unexpected formation of a 1,3-imino-heptitol derivative

The NIS-mediated iodocyclization of 4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-1,2,3-trideoxy-D-gluco-hept-1-enitol gave unexpectedly a 1,3-imino-heptitol derivative, namely 2-O-acetyl-N-benzyl-4,5,7-tri-O-benzyl-1,3-dideoxy-1,3-imino-D-glycero-D- ido-heptitol. This compound is a new example of a rare class of azetidine imino alditol derivatives which have interesting properties such as glycosidase inhibitors. The physical and spectral data for this imino heptitol were essentially identical to those reported for 2,6-anhydro-4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-3-deoxy-D-glycero-D- ido-heptitol, a derivative of C-(2-acetamido-2-deoxy-α-D-glucopyranosyl)methanol obtained from the same precursor [Lay, L.; Nicotra, F.; Panza, L.; Verani, A. Gazz. Chim. Ital. 1992, 122, 345-348]; these findings cast doubts on the structure reported for the latter product.

Synthesis of azasugars by Grignard reaction on glycosylamines

Pyrrolidines 5a-b, and piperidines 10a,b and 15, were synthesised by Grignard reaction on a glycosylamine, easily obtained from the parent sugar and a primary amine, followed by cyclization with triflic anhydride.

A new procedure for the synthesis of azasugars

Reaction of the commercially available 2,3,5-tri-O-benzyl-D-arabinose with a primary amine (RNH2) affords the arabinofuranosylamine 2, which on treatment with a Grignard reagent stereoselectively gives the aminoalcohol 3. 3 is an useful precursor of azasugars: it is converted into the pyrrolidine 4 by treatment with Tf2O-Py, whereas by oxidation with PCC it affords the lactam 5 which can be reduced to the corresponding amine 6.