139404-79-8

Upstream product

• 139326-95-7 α/β-D-xylo-5-hexeno-furanose 
• 7284-07-3 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-eno-furanose 
• 43138-42-7 methyl 5,6-dideoxy-α-L-arabino-hex-5-enofuranoside 
• 87-72-9 L-(+)-arabinose 
• 143106-69-8 5,6-dideoxy-D-threo-hex-5-en-2-ulose 

Downstream Products

• 609-06-3 L-xylose 
• 107-02-8 acrolein 
• 5328-37-0 L-arabinose 

Relevant academic research and scientific papers

Substrate Specificity and Carbohydrate Synthesis Using Transketolase

This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis.The properties of transketolase from both yeast and spinach were investigated.The yeast enzyme was found to be more convenient for routine use.Examination of the substrate specificity of yeast tansketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates.A practical protocol for tansketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.

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.

Synthesis of 3,5-anhydro-2-deoxy-1,4-glyconolactones by palladium(II)-catalyzed, regioselective oxycarbonylation of C5- and C6-enitols. ω-Homologation of aldoses to produce intermediates for C-glycoside/C-nucleoside synthesis

The palladium(II)-catalyzed oxycarbonylation, known with alkenols and alkenediols, is studied with optically active 4-pentenitols (-triols) 1, 7 and 5-hexenitols (-tetrols) 12, 15, 18. Efficient routes for the substrates are provided, mostly from carbohyd