65530-21-4

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 79549-74-9 methyl 4,6-O-benzylidene-α-D-allopyranoside 

Downstream Products

• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 29845-75-8 methyl 4,6-O-benzylidene-3-O-methanesulfonyl-α-D-glucopyranoside 
• 18944-91-7 Benzoic acid (2S,3R,4S,5R,6S)-2-bromomethyl-4,5-bis-methanesulfonyloxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 
• 63598-31-2 methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 
• 22860-24-8 5-hydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diyl-dimethanesulfonate 
• 116003-77-1 2-azido-2-deoxy-4,6-O-(phenylmethylene)methyl-α-D-altropyranoside 
• 287719-31-7 methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside 
• 207506-27-2 methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(trifluoromethanesulfonyl)-α-D-altropyranoside 
• 1155874-64-8 methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 

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.

A scalable approach to obtaining orthogonally protected β-d-idopyranosides

A practical method to obtain orthogonally protected d-idopyranose from d-galactose has been developed, which is the first method to enable synthesis of the challenging β-d-idopyranoside linkage. The method relies on a key double inversion at O-2 and O-3 in an easily prepared d-galactose derivative, which proceeds regio- and stereoselectively through a 2,3-anhydrotalopyranoside; reaction using a selection of alkoxides affords exclusively the 3-O-alkylidopyranoside, which can be used to generate an orthogonally protected monosaccharide. The process is scalable and requires minimal purification, so it could be used to produce building blocks to aid in the synthesis of various β-idopyranose-containing oligosaccharide targets to further probe their biological functions.

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.

Synthesis of D-rubranitrose by using a novel method for constructing functionalized branched-chain structures

Convenient synthesis of D-rubranitrose from D-glucose was achieved by using simple and novel methods for deoxygenation and construction of functionalized branched-chain structures. The total yield of D-rubranitrose from methyl 4,6-O-benzylidene-α-D-glucop

Synthetic approach to tetrahydrofuran units and five-membered ring lactones fused to hexopyranosides

A stereoselective synthesis of the miharamycin sugar moiety epimer at C-3′ was accomplished in high yield starting from an appropriate (Z)-Wittig product, synthesized by Wittig reaction of a 4,6-O-benzylidene protected hexopyranosid-3-ulose with [(ethoxycarbonyl)methylene]triphenylphosphorane followed by iodine promoted isomerisation of the (E)-Wittig product formed. Reduction of the (Z)-isomer obtained in quantitative yield, cyclisation and dihydroxylation with osmium tetroxide, gave the target molecule containing a cis-fused tetrahydrofuran ring in its structure. Synhesis of five-membered rings trans-fused to the hexopyranosidic units succeeded via two different synthetic pathways. Stereoselective Reformatsky reaction of a 2,6-di-O-pivaloyl protected hexopyranosid-3-ulose, followed by cyclisation with dimethylzinc gave a 3,4-trans-fused lactone. The approach using the reaction of 2,3-and 3,4-epoxides with the dianion of phenylselenoacetic acid led to low yield but novel phenylseleno derivatives of trans-fused five-membered rings, namely a phenylselenolactone 2,3-trans-fused to a 4,6-O-benzylidene-hexopyranoside and a phenylselenolactenol 3,4-trans-fused to a 6-O-pivaloyl-hexopyranoside.

STEREOSELECTIVE SYNTHESIS OF(-)-α-MULTISTRIATIN FROM D-GLUCOSE

D-glucose was converted into (-)-α-multistriatin, the aggregation pheromone of the Europian elm bark beetle, via a highly stereoselective eighteen-step route