117249-17-9

Upstream product

• 100-39-0 benzyl bromide 
• 53657-42-4 L-rhamnal 
• 100-44-7 benzyl chloride 
• 34819-86-8 3,4-di-O-acetyl-6-deoxy-L-glucal 
• 106848-97-9 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl bromide 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 73-34-7 L-rhamnose 

Downstream Products

• 162332-12-9 (1R,3S,4S,5S,6S)-4,5-Bis-benzyloxy-3-methyl-2-oxa-bicyclo[4.1.0]heptane 
• 149561-65-9 (-)-(2S,3S)-3-(Benzyloxy)-2-methyl-2,3-dihydro-4H-pyran-4-one 
• 154779-60-9 1,2-anhydro-3,4-di-O-benzyl-6-deoxy-α-L-glucopyranose 
• 79080-88-9 3,4-di-O-benzyl-6-deoxy-α-L-mannopyranose 
• 78161-49-6 3,4-di-O-benzyl-L-rhamnopyranose 
• 69558-07-2 methyl-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 111723-26-3 methyl 3,4-di-O-benzyl-β-L-quinovopyranoside 

Relevant academic research and scientific papers

Electrochemical Trifluoromethylation of Glycals

Carbohydrates play essential roles in various physiological and pathological processes. Trifluoromethylated compounds have wide applications in the field of medicinal chemistry. Herein, we report a practical and efficient trifluoromethylation of glycals b

Ir(I)-Catalyzed C?H Glycosylation for Synthesis of 2-Indolyl-C-Deoxyglycosides

The construction of 2-deoxy-C-glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2-indolyl-C-deoxyglycosides via Ir(I)-catalyzed, pyridine-group-directed C?H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β-configuration products. Gram-scale synthesis and several practical transformations were conducted for further applications. Meantime, we also explored the mechanism of this method and proposed a catalytic cycle. (Figure presented.).

Tuning the Chemoselectivity of Silyl Protected Rhamnals by Temperature and Br?nsted Acidity: Kinetically Controlled 1,2-Addition vs Thermodynamically Controlled Ferrier Rearrangement

An acidity- and temperature-dependent chemoselective glycosylation of silyl-protected rhamnals with alcohols has been revealed. The reaction undergoes a 1,2-addition pathway with (±)-CSA as the catalyst at rt, affording kinetically controlled 2-deoxyl rhamnosides. In contrast, only thermodynamically controlled 2,3-unsaturated rhamnosides are formed via Ferrier rearrangement when elevating reaction temperature to 85 °C or using CF3SO3H instead. This tunable glycosylation allows facile and practical access to both 2-deoxyl and 2,3-unsaturated rhamnosides with excellent yields and high α-stereoselectivity.

Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature

A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including d-glucal, d-galactal, l-rhamnal, d-xylal and d-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.

MACROCYCLIC PICOLINAMIDE COMPOUNDS WITH FUNGICIDAL ACTIVITY

This disclosure relates to macrocyclic picolinamides of Formula (I) and their use as fungicides.

Fluorine-directed 1,2-trans glycosylation of rare sugars

To reconcile the urgent need to access well defined β-configured 2,6-di-deoxypyranose analogues for chemical biology, with the intrinsic α-selectivity of the native system, the directing role of fluorine at C2 has been explored. Localised partial charge inversion (C-Hδ+ → C-Fδ-) elicits a reversal of the substrate-based α-stereoselectivity, irrespective of the protecting group electronics.

Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis

A mild, efficient, and practical transformation for the direct C-H trifluoromethylation of glycals under visible light has been reported for the first time. This reaction employed fac-Ir3+(ppy)3 as the photocatalyst, Umemoto's reagent as the CF3 source, and a household blue LED or sunlight as the light source. Glycals bearing both electron-withdrawing and -donating protective groups performed this reaction smoothly. This visible light-mediated trifluoromethylation reaction was highlighted by the trifluoromethylation of the biologically important Neu2en moiety.

MACROCYCLIC PICOLINAMIDES AS FUNGICIDES

The disclosure relates to macrocyclic picolinamides of Formula (I) and to the use of these compounds as fungicides.

Preparation of C-arylglycals via Suzuki–Miyaura cross-coupling of dihydropyranylphosphates

The preparation of C-arylglycals has been accomplished by employing the Suzuki–Miyaura cross-coupling reaction of dihydropyranylphosphates with arylboronate esters. The reaction is tolerant of both electron-donating (EDG) and electron-withdrawing (EWG) gr

Copper catalyzed β-difluoroacetylation of dihydropyrans and glycals by means of direct C-H functionalization

A copper catalyzed direct functionalization of dihydropyrans and glycals has been developed. This method affords a new and straightforward access to C-2-CF2 dihydropyrans and glycosides in a single step starting from readily available starting