15814-59-2

Upstream product

• 67-56-1 methanol 
• 2438-80-4 L-Fucose 
• 73-34-7 6-deoxy-L-galactose 
• 7512-03-0 methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-D-mannopyranoside 
• 131089-34-4 3-O-benzoyl-6-O-(t-butyldiphenyl)silyl-α-D-mannopyranoside 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 65518-53-8 methyl 2,3,4-tri-O-benzyl-6-O-tosyl-α-D-mannopyranoside 
• 33639-74-6 methyl 2,3,4-tri-O-benzyl-α-D-rhamnopyranoside 
• 92418-38-7 (3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate 
• 6340-57-4 methyl 2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranoside 
• 111476-43-8 methyl β-D-glucopyranoside 6-phenylthionocarbonate 
• 73-34-7 D-Fucose 
• 150650-49-0 methyl 2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-β-D-galactopyranoside 
• 96048-23-6 methyl-2-O-α-L-rhamnopyranosyl-β-D-fucopyranoside 

Downstream Products

• 14064-39-2 L-galacto-2,4,5-Trihydroxy-3-methoxy-hexanal 
• 1379777-16-8 methyl 3-O-phenoxythiocarbonyl-β-L-fucopyranoside 
• 1399293-50-5 methyl 3-O-(3,5-difluorobenzensulfonyl)-β-L-fucopyranoside 
• 1128-40-1 methyl 6-deoxy-β-L-glucopyranoside 
• 1128-40-1 methyl-α-DL-rhamnopyranoside 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-D-rhamnopyranoside 
• 634-74-2 D-rhamnose 
• 135216-52-3 methyl 2,3-di-O-benzoyl-6-deoxy-4-O-<(p-nitrophenyl)sulfonyl>-α-D-mannopyranoside 
• 134311-92-5 methyl-2,4-di-O-benzyl-β-D-quinovopyranoside 
• 176380-03-3 methyl 2,3‐di‐O‐benzyl‐6‐deoxy‐β‐D‐glucopyranoside 
• 197657-27-5 methyl-2-O-benzyl-β-D-quinovopyranoside 
• 51288-33-6 C₂₁H₂₂O₇ 
• 51236-57-8 C₂₁H₂₂O₇ 
• 3615-37-0 D-Fucose 

Relevant academic research and scientific papers

Synthesis of modified D-mannose core derivatives and their impact on GH38 α-mannosidases

Nine new compounds having five- and modified six-member carbohydrate core derived from D-lyxose or D-mannose, and non-hydrolysable aglycones (benzylsulfonyl or aryl(alkyl)triazolyl) were synthesised to investigate their ability to inhibit the recombinant

Calcium hypophosphite mediated deiodination in water: Mechanistic insights and applications in large scale syntheses of d-quinovose and d-rhamnose

The inorganic calcium hypophosphite was found to be a cheap, non-toxic, water-soluble and environmentally friendly reducing reagent for radical deiodination in water. Thorough mechanism studies revealed that calcium hypophosphite was oxidized to water insoluble calcium phosphite which was the major co-product of the deiodination reaction. Based on this observation, a practical synthesis of rare d-quinovose and d-rhamnose from cheap and commercially available materials on a hundred-mmol scale was reported.

The structure of the O-specific polysaccharide from Ralstonia pickettii

The following structure of the Ralstonia pickettii have been determined using NMR and chemical methods:→4)-α-D-Rha-(1→4)-α-L- GalNAcA-(1→3)-β-D-BacNAc-(1→

Total Synthesis of Tiacumicin A. Total Synthesis, Relay Synthesis, and Degradation Studies of Fidaxomicin (Tiacumicin B, Lipiarmycin A3)

The commercial macrolide antibiotic fidaxomicin was synthesized in a highly convergent manner. Salient features of this synthesis include a β-selective noviosylation, a β-selective rhamnosylation, a ring-closing metathesis, a Suzuki coupling, and a vinylo

Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation

A Cu(II)-catalyzed diastereoselective Michael/aldol cascade approach is used to accomplish concise total syntheses of cardiotonic steroids with varying degrees of oxygenation including cardenolides ouabagenin, sarmentologenin, 19-hydroxysarmentogenin, and 5-epi-panogenin. These syntheses enabled the subsequent structure activity relationship (SAR) studies on 37 synthetic and natural steroids to elucidate the effect of oxygenation, stereochemistry, C3-glycosylation, and C17-heterocyclic ring. Based on this parallel evaluation of synthetic and natural steroids and their derivatives, glycosylated steroids cannogenol-l-α-rhamnoside (79a), strophanthidol-l-α-rhamnoside (92), and digitoxigenin-l-α-rhamnoside (97) were identified as the most potent steroids demonstrating broad anticancer activity at 10-100 nM concentrations and selectivity (nontoxic at 3 μM against NIH-3T3, MEF, and developing fish embryos). Further analyses indicate that these molecules show a general mode of anticancer activity involving DNA-damage upregulation that subsequently induces apoptosis.

Synthesis of Deoxyglycosides by Desulfurization under UV Light

This study was performed to develop a highly efficient method whereby desulfurization could be completed in 0.5 h under ultraviolet light, at room temperature, and in the presence of trialkylphosphine. Using this method, deoxyglycosides could be produced from sulfur-containing glycosides in almost quantitative yields. The much higher reactivity of desulfurization with triethylphosphine versus that with triethylphosphite is also discussed.

Synthesis of β-(1→2)-Linked 6-Deoxy- l -altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor

The β-(1→2)-linked 6-deoxy-l-altropyranose di- to pentasaccharides 2-5, relevant to the O-antigen of the infectious Yersinia enterocolitica O:3, were synthesized for the first time. The challenging 1,2-cis-altropyranosyl linkage was assembled effectively via glycosylation with 2-O-benzyl-3,4-di-O-benzoyl-6-deoxy-l-altropyranosyl ortho-hexynylbenzoate (7) under the catalysis of PPh3AuNTf2. NMR and molecular modeling studies showed that the pentasaccharide (5) adopted a left-handed helical conformation.

Direct glycosylation of unprotected and unactivated sugars using bismuth nitrate pentahydrate

Bi(NO3)3, a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high α-selectivity. Further, an expedient separation of α- and β-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.

Total Synthesis of the Glycosylated Macrolide Antibiotic Fidaxomicin

The first enantioselective total synthesis of fidaxomicin, also known as tiacumicin B or lipiarmycin A3, is reported. This novel glycosylated macrolide antibiotic is used in the clinic for the treatment of Clostridium difficile infections. Key features of

Catalytic and regioselective oxidation of carbohydrates to synthesize keto-sugars under mild conditions

A new catalytic and regioselective approach for the synthesis of keto-sugars is described. An organotin catalyst, Oc2SnCl2, in the presence of trimethylphenylammonium tribromide ([TMPhA]+Br3-) accelerates the regioselective oxidation at the axial -OH group of 1,2-diol moieties in galactopyranosides. The reaction conditions can also be used for the regioselective oxidation of various carbohydrates.