14686-88-5

Usage

Chemical Properties

White Crystalline Solid

InChI:InChI=1/C14H20O7/c1-7(15)17-10-9(8-6-16-13(2,3)19-8)18-12-11(10)20-14(4,5)21-12/h8,11-12H,6H2,1-5H3/t8?,11?,12-/m1/s1

Upstream product

• 10578-85-5 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose hydrate 
• 108-24-7 acetic anhydride 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 492-62-6 alpha-D-glucopyranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-D-glucofuranoside 
• 2280-44-6 D-Glucose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 

Downstream Products

• 14086-88-5 3-Acetylamino-3-desoxy-α-D-galaktopyranose 
• 35023-80-4 (Z)-2,3:5,6-di-O-isopropylidene-D-gulose oxime 
• 35023-80-4 (E)-2,3:5,6-di-O-isopropylidene-D-gulose oxime 
• 237749-86-9 (2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol 
• 340699-20-9 (6R,7S,8S)-8-Benzyloxy-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine-6,7-diol 
• 23885-38-3 3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranoside 
• 16713-80-7 3-O-acetyl-1,2:5,6-di-isopropylidene-α-D-gulofuranose 

Relevant academic research and scientific papers

Synthesis of Uridine 5′-[2-S-Pyridyl-3-thio-α -D-galactopyranosyl Diphosphate]: Precursor of UDP-Thiogal Sugar Nucleotide Donor Substrate for β-1,4-Galactosyltransferase

The syntheses of a novel uridine diphosphate galactose (UDP-Gal) analog, (UDP-2,4,6-tri-O-acetyl-3-S-acetyl-3-thio-α-D-galactopyranose) (11) and the thiolpyridine protected (Uridine 5′-[3-S-(2-S-pyridyl)-3-thio-α -D-galactopyranosyldiphosphate) analog (12) are described. The reported synthesis relies on the novel use of thiolpyridine to generate 12 which is a suitably protected intermediate for generating a UDP-thioGal derivative by reduction prior to enzyme transfer via β-1,4-galactosyltransferase.

Functional saccharide molecule based on TDG molecular skeleton and preparation method thereof

The invention discloses a functional saccharide molecule based on a TDG molecular skeleton. A carbohydrate compound is designed, and the structure of the carbohydrate compound is shown in a formula X, wherein R1 and R2 are independently selected from substituted acylamino, substituted triazolyl and substituted amino, R3 is selected from sulfydryl, azido, amino and carboxyl, A is -CmH2mR3, X is selected from an oxygen atom, n is selected from 0, 1, 2, 3, 4, 5, 6 and 7, and m is selected from 2, 3, 4, 5, 6, 7, 8, 9 and 10. According to the invention, a synthesis strategy of side chain derivatization first and glycosylation coupling later is adopted, so that side chain derivatization modification of the TDG molecular skeleton is realized, and efficient synthesis of the compound is realized. TDG sugar ligand molecules are used for recognizing and combining target proteins, the function of the TDG sugar ligand molecules as a target head as regards recognizing and combining the target proteins is achieved, and the TDG sugar ligand molecules serve as target head molecules to construct functional targeting molecules, which have wide application prospects in the fields of tumor detection, tumor immunity and the like.

LARGE SCALE PROCESS FOR PREPARING 1,2,4, 6-TETRA-0-ACETYL-3-AZID0-3-DE0XY-D-GALACT0PYRAN0SIDE

The present invention relates to a process for preparing a compound of formula (X), wherein said process is suitable for large scale synthesis.

Reversal of Stereoselectivity in Cycloadditions of Five-Membered Cyclic Nitrones Derived from Hexoses

Two five-membered cyclic nitrones derived from hexoses, a newly synthesized d-allo-configured nitrone and an already known d-talo-configured nitrone, have been examined in 1,3-dipolar cycloaddition reactions with vinyl acetate, allyl benzoate, methyl acrylate, acrylonitrile, and vinylene carbonate. The reactions of the d-allo-configured nitrone proceeded preferentially through the expected exo-anti transition state, but all the cycloadditions of the d-talo-configured nitrone surprisingly showed high exo-syn selectivity. This reversal of stereoselectivity has been explained by 3D analysis of the preferred conformations of the nitrones, obtained from X-ray data. The structures were further inspected using CONFLEX, PM5, and DFT calculations. All these methods revealed that the dioxolane substituents attached to C-5 of both nitrones had opposite spatial locations.

Synthesis of a MUC1-glycopeptide-BSA conjugate vaccine bearing the 3′-deoxy-3′-fluoro-Thomsen-Friedenreich antigen

A novel MUC1-glycopeptide-BSA conjugate vaccine with a specifically fluorinated Thomsen-Friedenreich antigen side chain at Thr6 was prepared. Preliminary immunological experiments reveal specific binding of the tumor-associated glycopeptide antigen analog by anti-MUC1-mouse antibodies.

Synthesis and evaluation of 3″- and 4″-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000

Four 3″- and 4″-deoxy and -fluorogalactosyl ceramides were synthesized, and their ability to stimulate iNKT cells, based on levels of IL-2 production, was assessed in three NKT cell receptor hybridomas. In two of the hybridomas, 1.2 and 2H4, all of the analogs were immunostimulatory, while in the 1.4 hybridoma only the 4″-fluoro analog led to the production of significant levels of IL-2.

MATRIX METALLOPROTEINASE INHIBITORS

The present invention relates to β-hydroxy and amino substituted carboxylic acids, which act as matrix metalloprotease inhibitors, particularly diastereomerically pure β-hydroxy carboxylic acids, corresponding processes for the synthesis of and pharmaceutical compositions containing the compounds of the present invention. Compounds of the present invention are useful in the treatment of various inflammatory, autoimmune and allergic diseases, such as methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatic arthritis, psoriasis, pulmonary fibrosis, wound healing disorders, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, neointimal proliferation, which leads to restenosis and ischemic heart failure, stroke, renal diseases, tumor metastasis, and other inflammatory disorders characterized by the over-expression and over- activation of a matrix metalloproteinase using the compounds.

Improved double epimerisation of (D)-glucose into (D)-gulose and the synthesis of (D)-xylo-imidazolopiperidinose

Rhodium/alumina catalysed cis-hydrogenation of the known enol-acetate 7 proceeded quantitatively and with complete stereoselectivity leading to the D-gulose derivative 8. Several reaction steps permitted transformation of 8 into the target D-xylo-imidazolopiperidinose ent-4 molecule, i.e, the enantiomer of the already known imidazolo-sugar 4.

3-Azidotetrahydrofuran-2-carboxylates: Monomers for five-ring templated β-amino acid foldamers?

Four diastereomeric methyl 3-azidotetrahydrofuran-2-carboxylates were prepared from diacetone glucose as precursors for the synthesis of β-amino acid oligomers with secondary structure.

A new Approach to 3-Acetylamino-3-desoxy-D-galactose

The synthesis of the title compound from 1,2:5,6-Di-O-isopropyliden-α-D-glucofuranose (1) via 1,2:5,6-Di-O-isopropyliden-α-D-gulofuranose (4) is reported.The key-step is the introduction of the azido function into 4 which is achieved by using Triphenylphosphane/Diethylazodicarboxylate/HN3. - Keywords: 3-Acetylamino-3-desoxy-D-galactose, syntheses of; TPP-DEAD-HN3, reaction with 1,2:5,6-Di-O-isopropyliden-α-D-gulofuranose