92574-56-6

Upstream product

• 59-23-4 D-Galactose 
• 43138-42-7 methyl 5,6-dideoxy-α-L-arabino-hex-5-enofuranoside 
• 87-72-9 L-(+)-arabinose 

Downstream Products

• 5328-37-0 L-arabinose 
• 107-02-8 acrolein 

Relevant academic research and scientific papers

Seven-Step Synthesis of All-Nitrogenated Sugar Derivatives Using Sequential Overman Rearrangements

All-nitrogenated sugars (ANSs), in which all hydroxy groups in a carbohydrate are replaced with amino groups, are anticipated to be privileged structures with useful biological activities. However, ANS synthesis has been challenging due to the difficulty in the installation of multi-amino groups. We report herein the development of a concise synthetic route to peracetylated ANSs in seven steps from commercially available monosaccharides. The key to success is the use of the sequential Overman rearrangement, which enables formal simultaneous substitution of four or five hydroxy groups in monosaccharides with amino groups. A variety of ANSs are available through the same reaction sequence starting from different initial monosaccharides by chirality transfer of secondary alcohols. Transformations of the resulting peracetylated ANSs such as glycosylation and deacetylation are also demonstrated. Biological studies reveal that ANS-modified cholesterol show cytotoxicity against human cancer cell lines, whereas each ANS and cholesterol have no cytotoxicity.

HYDRAZINOLYSIS OF MONOSACCHARIDES: A TWO-STEP SYNTHESIS OF CHIRAL PENTANE-1,2,3-TRIOLS FROM PENTOSES AND OBSERVATIONS ON THE HYDRAZINOLYSIS OF GLYCOPROTEINS AND GLYCOPEPTIDES

1,2-Dideoxyalditols, the corresponding 1-alkenes, and 1-deoxyalditols are formed in various proportions from D-glucose, D-mannose, L-arabinose, and D-xylose by the action of refluxing hydrazine.Sequential hydrazinolysis, catalytic hydrogenation, and chromatography afford a route to 1,2-dideoxyalditols.For example, 1,2-dideoxy-L-erythro-pentitol is formed from L-arabinose in 42percent yield, and D-xylose is a source of 1,2-dideoxy-D-threo-pentitol (50percent).Under the conditions (anhydrous hydrazine at 100 deg C for 30 h in the absence of air) used Montreuil for the hydrazinolysis of glycoproteins and glycopeptides, no 1,2-dideoxialditol was formed; degradation was incomplete, there being some aldose hydrazone present.Under Kochetkov's hydrazinolysis conditions (105 deg C for 10 h with hydrazinium sulphate), less degradation occured and product from D-galactose was identified as 1-deoxy-D-tagatose hydrazone.