686298-97-5

Upstream product

• 14685-78-0 methyl-(2-chloro-2-deoxy-β-D-glucopyranoside) 
• 2880-98-0 methyl-(2-bromo-2-deoxy-β-D-glucopyranoside) 
• 75556-27-3 2,3,4-Tri-O-acetyl-1,5-anhydro-6-deoxy-L-arabino-hex-1-enitol 
• 20771-15-7 methyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 3258-19-3 methyl-(2,3-anhydro-β-D-talopyranoside) 
• 134235-73-7 methyl 3-azido-3-deoxy-β-D-allopyranoside 
• 17690-23-2 methyl-[O²,O⁴,O⁶-triacetyl-O³-(toluene-4-sulfonyl)-β-D-glucopyranoside] 
• 4631-21-4 methyl 3-nitro-β-D-3-deoxy-glucopyranoside 
• 17460-41-2 methyl-[O²,O⁴,O⁶-triacetyl-O³-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 127258-07-5 methyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 60844-86-2 methyl 3-deoxy-3-methoxyimino-α-D-ribo-hexopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 16977-86-9 methyl-α-D-ribo-hexapyranoside-3-ulose 
• 58479-62-2 (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

Stereoselective Protection-Free Modification of 3-Keto-saccharides

Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.

Arynes in the Monoarylation of Unprotected Carbohydrate Amines

A CsF-mediated method has been developed for the N-arylation of amino sugars that affords good to excellent yields of arylated products under mild conditions involving the in situ generation of arynes. The reaction conditions tolerate a variety of common carbohydrate protecting groups and also performs exceptionally well on unprotected amino sugar derivatives. The reactions are scalable in moderate to good yields with broad scope.

Osmium-catalyzed tethered aminohydroxylation of glycals: A stereodirected access to 2- and 3-aminosugars

The osmium-catalyzed aminohydroxylation of glycals has been achieved with complete regio- and stereocontrol by taking advantage of the Donohoe tethering approach. Glucals and galactals showed complementary reactivity in dependence of the stage at which the reaction was performed, i.e., directly or after double-bond shift consequent to a Ferrier rearrangement (that is, on the 1,2 or 2,3-unsaturated sugar), allowing access to both classes of 2-amino (mannosamine) and 3-amino (talosamine) sugar derivatives, respectively.

Modulating weak interactions for molecular recognition: A dynamic combinatorial analysis for assessing the contribution of electrostatics to the stability of CH-π bonds in water

Electrostatic and charge-transfer contributions to CH-π complexes can be modulated by attaching electron-withdrawing substituents to the carbon atom. While clearly stabilizing in the gas phase, the outcome of this chemical modification in water is more difficult to predict. Herein we provide a definitive and quantitative answer to this question employing a simple strategy based on dynamic combinatorial chemistry.

SELECTIVE OXIDATION OF CARBOHYDRATES

The invention relates to the field of carbohydrate chemistry. Provided is a process for the regioselective oxidation of a single secondary hydroxy function of a carbohydrate substrate comprising two or more secondary hydroxy functions, comprising contacting the carbohydrate substrate in a solvent in the presence of a transition metal catalyst complex with an oxidizing agent to yield a mono-oxidized carbohydrate.

Catalytic regioselective oxidation of glycosides

Discrimination among equals: A catalytic method for the selective oxidation of unprotected glycosides, both monosaccharides and disaccharides, has been developed. The resulting ketosaccharides are isolated in moderate to excellent yields. This approach provides a basis for protecting-group-free synthetic transformations of carbohydrates. Copyright

A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-d-glucitol

3-Acetamido-5-amino-3,5,6-trideoxy-d-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-d-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-β-d-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale.

Synthesis of the methyl 3-amino-3-deoxy-α- and β-D-allopyranosides and -allofuranosides

Methyl 3-amino-3-deoxy-α-D-allopyranoside was synthesized from methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside in a 5-step sequence involving trifluoromethylsulfonylation, azide displacement, deprotection, and catalytic hydrogenation.On displacem

Rearrangement of Carbohydrate Epoxides to Amino Sugars Using a Trichloroacetimidoyl Neighboring Group

When glycosides containing an epoxide functionality are treated with trichloroacetonitrile and sodium hydride, the free hydroxy groups are converted into trichloroacetimidates, which subsequently open the epoxide ring to give aminosugar derivatives.The re