287719-31-7

Upstream product

• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 65530-21-4 methyl 4,6-O-benzylidene-2,3-di-O-methanesulfonyl-α-D-glucopyranoside 
• 116003-77-1 2-azido-2-deoxy-4,6-O-(phenylmethylene)methyl-α-D-altropyranoside 
• 207506-27-2 methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(trifluoromethanesulfonyl)-α-D-altropyranoside 

Downstream Products

• 1155874-64-8 methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside 
• 287719-33-9 Acetic acid (2R,3S,4R,5S,6S)-4,5-diazido-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 6410-50-0 methyl 4,6-di-O-acetyl-2,3-diazido-2,3-dideoxy-α-D-mannopyranoside 

Relevant academic research and scientific papers

Diaminohexopyranosides as ligands in half-sandwich ruthenium(II), rhodium(III), and iridium(III) complexes

The syntheses of methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-d-hexopyranosides of glucose, mannose, gulose, and talose and methyl 2-amino-4,6-benzylidene-2,3-dideoxy-3-tosylamido-α-d-glucopyranoside are exhaustively presented, as well as their application as ligands in half-sandwich ruthenium(II), rhodium(III), and iridium(III) complexes. The complex formation occurs highly diastereoselectively, creating a stereogenic metal center. The molecular structures of the ligands and their complexes were investigated by X-ray structure analysis, NMR spectroscopy, polarimetry, and DFT methods. The diamino monosaccharide complexes have been subjected to antitumor activity studies. In vitro tests of a few ruthenium complexes against different cancer cell types showed antiproliferative activities 4-10 times lower than that of cisplatin.

Stereoselective synthesis of 2,3-diamino-2,3-dideoxy-β-d- mannopyranosyl uronates

With the aim to find an efficient synthetic procedure for the construction of 2,3-diamino-2,3-dideoxy-β-d-mannuronic acids, we evaluated three mannosyl donors: (S)-phenyl 4,6-di-O-acetyl-2,3-diazido mannopyranoside, (S)-phenyl 2,3-diazido-4,6-O-benzylidene mannopyranoside, and (S)-phenyl 2,3-diazido mannopyranosyl methyl uronate. The first two mannosylating agents are rather unselective or slightly α-selective in their condensation with three different acceptors. The mannuronic acid donor on the other hand reliably provides the desired β-mannosidic linkage. A mechanistic rationale is put forward to account for the different behavior of the three donor types. Suitably protected 2,3-diazido mannuronic acids were employed to construct the all-cis-linked tetrasaccharide repeating unit of the capsular polysaccharide of Bacillus stearothermophilus, featuring two 2,3-diacetamido-2,3-dideoxy-β-d- mannuronic acids.

Aldotetroses and C(3)-Modified Aldohexoses as Substrates for N-Acetylneuraminic Acid Aldolase: A Model for the Explanation of the Normal and the Inversed Stereoselectivity

The four stereoisomeric aldotetroses were accepted with different reactivities by N-acetylneuraminic acid aldolase.C(3)-modified D-mannose and D-glucose derivatives, respectively, failed to undergo enzymatic aldol addition.Based on the observed reactivities of the tested compounds (about 58), a mechanistic scheme is proposed which relates substrate structure, reactivity and stereochemical outcome observed in Neu5Ac aldolase-catalyzed reactions.The condensation products obtained in the L-erythrose and D-threose reactions are side-chain modified sialic acid and D-KDO derivatives, respectively, of biological interest.