469873-52-7

Upstream product

• 10257-28-0 D-Galactose 
• 123-54-6 acetylacetone 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 59-23-4 D-Galactose 
• 7296-64-2 β-D-galactopyranoside 
• 87-81-0 D-tagatose 
• 67-64-1 acetone 
• 853269-40-6 5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose 

Downstream Products

• 1296138-39-0 4-butyl-5-pentyl-2-((2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)cyclohex-2-enone 
• 1355214-20-8 1-C-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)propan-2-one ethylene ketal 
• 1355357-75-3 2-(1-C-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)methyl)propene 
• 1419923-66-2 (E)-1-(β-D-galactopyranosyl)-4-(4-hydroxyphenyl)but-3-en-2-one 
• 1419923-60-6 (E)-1-β-D-galactopyranosyl-4-(3-hydroxyphenyl)but-3-en-2-one 
• 1419923-40-2 (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-4-(4-hydroxyphenyl)but-3-en-2-one 
• 1419923-33-3 (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-4-(3-hydroxyphenyl)but-3-en-2-one 
• 1314797-66-4 C₂₀H₂₀ClNO₉ 
• 1314797-74-4 C₁₈H₂₅NO₆ 
• 1314797-81-3 C₂₂H₂₄O₆ 
• 1314797-73-3 C₁₇H₂₀O₈ 

Relevant academic research and scientific papers

Synthesis and evaluation of C-glycosides as hydrotropes and solubilizing agents

This work presents expeditious synthesis of C-glycoside amphiphiles in aqueous media from unprotected di- or mono-saccharides. A Horner-Wadsworth- Emmons/Michael addition/Barbier allylation sequence led to C-glycosides that exhibit hydrotropic properties. The hydrotropic and solubilizing properties of these homoallylic alcohols including a β-C-glycoside moiety as well as additional β-C-glycosidic ketones with a short (C7) alkyl chain are also described and compared with those of commercial O-glucoside references.

Horner-wadsworth-emmons reaction of unprotected sugars in water or in the absence of any solvent: One-step access to C-glycoside amphiphiles

The synthesis of C-glycosides in water or in the absence of any solvent from free sugars and β-keto phosphonates is reported. The methodology permits a one-step access to C-glycoside amphiphiles in moderate-to-good yields. The selectivity (??/β and furanoside/pyranoside) is discussed and a process that leads to pure β-C-pyranosides is also described.

Regioselective facile one-pot Friedl?nder synthesis of sugar-based heterocyclic biomolecules

Regioselective facile one-pot synthesis of 16 different sugar-based quinoline, naphthyridine, and xanthone derivatives is reported. The compounds are characterized by NMR spectroscopy and elemental analysis. The β-Anomeric form of the sugar moiety was ide

One-step synthesis of β-C-glycosidic ketones in aqueous media: The case of 2-acetamido sugars

The one step synthesis of β-D-C-glycosidic ketones by condensation of pentane-2,4-dione with unprotected N-acetyl-D-gluco-, manno-, and galactosamine in alkaline aqueous media has been explored. N-Acetyl-D-gluco- and mannosamine gave, in good yield, a mixture of the two gluco and manno C-glycosidic ketones, which were separated by crystallization after acetylation, whereas N-acetyl-D-galactosamine afforded the galacto C-glycosidic ketone which was isolated as its acetylated derivative in 50% yield.

SYNTHESIS OF C-GLYCOSIDES OF INTEREST

The present invention relates to a biotechnological method for producing a C-glycoside of interest. The invention further relates to the use of a sialylated C-glycoside as a donor in an enzymatic glycosylation reaction. The present invention further relates to the following C- glycosides.

Synthesis of Reverse Glycosyl Fluorides and Rare Glycosyl Fluorides Enabled by Radical Decarboxylative Fluorination of Uronic Acids

An efficient protocol for synthesizing reverse glycosyl fluorides is described, relying on silver-promoted decarboxylative fluorination of structurally diverse pentofuran- and hexopyranuronic acids under the mild reaction conditions. The potential applications of the reaction are further demonstrated by converting readily available d-uronic acid derivatives into uncommon d-/l-glycosyl fluorides through a C1-to-C5 switch strategy. The reaction mechanism is corroborated by 5-exo-trig radical cyclization of allyl α-d-C-glucopyranuronic acid triggered by decarboxylative fluorination.

Synthesis of C-glycosylmethyl isoxazoles via aerobic oxidation of ketoximes catalyzed by TEMPO

An efficient and high yielding synthesis of C-glycosylmethyl isoxazoles by oxidation of ketoximes in the presence of oxygen and mediated by TEMPO is described.

Cascade Reactions of Unprotected Ketoses with Ketones – A Stereoselective Access to C-Glycosides

A highly stereoselective de-Bruyn–Ekenstein rearrangement/aldol condensation/intramolecular oxa-Michael cascade reaction of unprotected ketoses with ketones was elaborated. By the utilization of this new and operationally simple methodology an access to β-C-glycosides is given. Extremely matched and mismatched cases were observed by using with natural or unnatural proline in these cascade reactions.

GLYCOLIPIDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR USE IN THERAPY

A compound of Formula I: R1 -L1 -C(A)(A') - CH2, - L2-R2 or a pharmaceutically acceptable salt thereof, for use in medicine, for example in the treatment of a disease or condition selected from the group comprising cancer, autistic spectrum disorders. Alzheimer' s disease, Parkinson's disease, Huntingdon' s disease, muscie wasting and viral infection, wherein: R1 is selected from a carbohydrate group or derivative thereof, hydrogen, a C1-C24 alkyl or a C1-C24 derivative of an alkyl group, a C2-C24 alkenyl or a C2-C24 derivative of an aikenyl group, and a C2-C24 alkynyl group or a C2-C24 derivative of an alkynyl group; L1 is a linking group; L2 is a linking group; R2 is selected from hydrogen, a C1-C24 alkyl or a C1-C24 derivative of an alkyl group, a C2-C24 alkenyl or a C2-C24 derivative of an alkenyl group, and a C2-C24 alkynyl group or a C2-C24 derivative of an alkynyl group; A is selected from hydrogen and a C1 -C6 alkyl group: A' is selected from hydrogen, a C3 -C6 alkyl group, and L3-R3; wherein L3 is a linking group; and R3 is selected from hydrogen, a C1-C24 alkyl or a C1-C24 derivative of an alkyl group, a C2-C24 alkenyl or a C2-C24 derivative of an alkenyl group, and a C2-C24 alkynyl group or a C2-C24 derivative of an alkynyl group; and wherein if A' is not L3-R3, then R2 is a C10-C24 alkyl or a C10-C24 derivative of an alkyl group, a C10-C24 alkenyl or a C10-C24 derivative of an alkenyl group, or a C10-C24 alkynyl group or a C10-C24 derivative of an alkynyl group; and wherein if A' is L3-R3, then one or both of R2 and R3 are a C10-C24 alkyl or a C10-C24 derivative of an alkyl group, a C10-C24 alkenyl or a C10-C24 derivative of an alkenyl group, or a C10-C24 alkynyl group or a C10-C24 derivative of an alkynyl group.

Attachment of carbohydrates to methoxyaryl moieties leads to highly selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII

The transmembrane isoforms of carbonic anhydrase (hCA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this paper, we present a new class of C-glycosides incorporating the me