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GLYCOCONJUGATES OF PHOSPHORAMIDATE ALKYLATORS FOR TREATMENT OF CANCER

Bromoglufosfamide and related compounds are useful in the treatment of cancer and other hyperproliferative diseases. Glufosfamide and bromoglufosfamide are synthesized by reacting the corresponding tetracetyl derivatives with MeOH and a catalytic amount of MeO(-). Tetraacetyl glufosfamide is obtained by reacting a tetraacetyl trichloroacetamidate intermediate of glucose, ifosfamide mustard, and an acid in an anhydrous polar solvent.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

A new application about 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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An efficient method for the preparation of glycosides with a free C-2 hydroxyl group from thioglycosides

A new and efficient method to produce glycosides with a free C-2 hydroxyl group through 1,2-acyl group migration which occurs during the hydrolysis of 4,6-benzylidene protected thioglycosides has been developed. The acyl transfer products allow for further elaboration.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Extracurricular laboratory:new discovery of 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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In an article, published in an article, once mentioned the application of 10343-06-3, Name is 2,3,4,6-Tetra-o-acetyl-D-glucopyranose,molecular formula is C14H20O10, is a conventional compound. this article was the specific content is as follows.Recommanded Product: 10343-06-3

New glycosidase activated nitric oxide donors: Glycose and 3-morphorlinosydnonimine conjugates

(Chemical Equation Presented) To achieve site specific delivery of nitric oxide (NO), a new class of glycosidase activated NO donors has been developed. Glucose, galactose, and N-acetylneuraminic acid were covalently coupled to 3-morphorlinosydnonimine (SIN-1), a mesoionic heterocyclic NO donor, via a carbamate linkage at the anomeric position. The beta-glycosides were successfully prepared for these conjugates, while the alpha-glycosidic compounds were very unstable. The new stable sugar-NO conjugates could release NO in the presence of glycosidases. Such NO prodrugs may be used as enzyme activated NO donors in biomedical research.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Chemistry is an experimental science, and the best way to enjoy it and learn about it is performing experiments.Introducing a new discovery about 10343-06-3, Name is 2,3,4,6-Tetra-o-acetyl-D-glucopyranose, category: Tetrahydropyrans.

Probing the influence of linker length and flexibility in the design and synthesis of new trehalase inhibitors

This work aims to synthesize new trehalase inhibitors selective towards the insect trehalase versus the porcine trehalase, in view of their application as potentially non-toxic insecticides and fungicides. The synthesis of a new pseudodisaccharide mimetic 8, by means of a stereoselective alpha-glucosylation of the key pyrrolizidine intermediate 13, was accomplished. The activity of compound 8 as trehalase inhibitor towards C. riparius trehalase was evaluated and the results showed that 8 was active in the muM range and showed a good selectivity towards the insect trehalase. To reduce the overall number of synthetic steps, simpler and more flexible disaccharide mimetics 9?11 bearing a pyrrolidine nucleus instead of the pyrrolizidine core were synthesized. The biological data showed the key role of the linker chain?s length in inducing inhibitory properties, since only compounds 9 (alpha,beta-mixture), bearing a two-carbon atom linker chain, maintained activity as trehalase inhibitors. A proper change in the glucosyl donor-protecting groups allowed the stereoselective synthesis of the beta-glucoside 9beta, which was active in the low micromolar range (IC50 = 0.78 muM) and 12-fold more potent (and more selective) than 9alpha towards the insect trehalase.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Archives for Chemistry Experiments of 10343-06-3

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10343-06-3, Name is 2,3,4,6-Tetra-o-acetyl-D-glucopyranose, molecular formula is C14H20O10, belongs to Tetrahydropyrans compound, is a common compound. In a patnet, once mentioned the new application about 10343-06-3, Recommanded Product: 10343-06-3

Glucosylquestiomycin, a novel antibiotic from Microbispora sp. TP-A0184: Fermentation, isolation, structure determination, synthesis and biological activities

Glucosylquestiomycin, a novel N-glucopyranoside of questiomycin A, was isolated from the culture broth of Microbispora sp. TP-A0184. The absolute configuration of the sugar was determined as D-configuration by chemical synthesis. The new antibiotic showed antibacterial activity against Gram-positive and -negative bacteria and yeasts and cytotoxic activity against U937 cells.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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The reactant in an enzyme-catalyzed reaction is called a substrate. Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction.I hope my blog about 10343-06-3 is helpful to your research., SDS of cas: 10343-06-3

The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.10343-06-3, Name is 2,3,4,6-Tetra-o-acetyl-D-glucopyranose, molecular formula is C14H20O10. In a Review£¬once mentioned of 10343-06-3, SDS of cas: 10343-06-3

Novel anthracycline-spacer-beta-glucuronide, -beta-glucoside, and -beta-galactoside prodrugs for application in selective chemotherapy

A series of anthracycline prodrugs containing an immolative spacer was synthesized for application in selective chemotherapy. The prodrugs having the general structure anthracycline-spacer-beta-glycoside were designed to be activated by beta-glucuronidase or beta-galactosidase. Prodrugs with -chloro, -bromo or -n-hexyl substituents on the spacer were synthesized as well as prodrugs containing a -beta-glucuronyl, -beta-glucosyl or -beta-galactosyl carbamate specifier. The key step in the synthesis of all prodrugs is the highly beta-diastereoselective addition reaction of the anomeric hydroxyl of a glycosyl donor to a spacer isocyanate resulting in the respective beta-glycosyl carbamate pro-moieties. The resulting protected pro-moieties were coupled to an anthracycline. Prodrugs were evaluated with respect to activation rate by the appropriate enzyme and additionally, their IC50 values were determined. Optimal prodrugs in this study were at least 100- to 200-fold less toxic than their corresponding drug in vitro and were activated to the parent drug in a half-life time of approximately 2h. Copyright (C) 1999 Elsevier Science Ltd.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Discovery of 10343-06-3

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A selective electrochemical method of glycosylation of 3beta-hydroxy-Delta5-steroids

A new electrochemical glycosylation method is presented. According to the method cholesterol and other 3beta-hydroxy-Delta5-steroids can be selectively transformed to glycosides using non-activated sugars. The method is also useful for the synthesis of glycoconjugates with sugar linked to a steroid moiety by an ether bond.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature

Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including alpha-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.

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Tetrahydropyran – Wikipedia,
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Glucoside derivatives of podophyllotoxin: Synthesis, physicochemical properties, and cytotoxicity

Background: Widespread concern of the side effects and the broad-spectrum anticancer property of podophyllotoxin as an antitumor agent highlight the need for the development of new podophyllotoxin derivatives. Although some per-butyrylated glucosides of podophyllotoxin and 4beta-triazolyl-podophyllotoxin glycosides show good anticancer activity, the per-acetylated/free of podophyllotoxin glucosides and their per-acetylated are not well studied. Methods: A few glucoside derivatives of PPT were synthesized and evaluated for their in vitro cytotoxic activities against five human cancer cell lines, HL-60 (leukemia), SMMC-7721 (hepatoma), A-549 (lung cancer), MCF-7 (breast cancer), and SW480 (colon cancer), as well as the normal human pulmonary epithelial cell line (BEAS-2B). In addition, we investigated the structure?activity relationship and the physicochemical property?anticancer activity relationship of these compounds. Results: Compound 6b shows the highest cytotoxic potency against all five cancer cell lines tested, with IC50 values ranging from 3.27¡À0.21 to 11.37¡À0.52 muM. We have also found that 6b displays higher selectivity than the etoposide except in the case of HL-60 cell line. The active compounds possess similar physicochemical properties: MSA > 900, %PSA < 20, ClogP > 2, MW > 700 Da, and RB > 10. Conclusion: We synthesized several glucoside derivatives of PPT and tested their cytotoxicity. Among them, compound 6b showed the highest cytotoxicity. Further studies including selectivity of active compounds have shown that the selectivity indexes of 6b are much greater than the etoposide except in the case of HL-60 cell line. The active compounds possessed similar physicochemical properties. This study indicates that active glucoside analogs of podophyllotoxin have potential as lead compounds for developing novel anticancer agents.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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A useful and convenient synthetic procedure for hydrolysis of thioglycosides

Various thioglycosides 1 are smoothly hydrolyzed chemo-selectively to the corresponding 1-hydroxy sugars 2 in good yields at 0-5C by employing (NH4)6Mo7O24¡¤ 4H2O-H2O2 or H2MoO4¡¤H2O-H2O2 to promote oxidation of ammonium bromide in the presence of perchloric acid in CH2Cl2-H2O solvent system. Mild conditions, good yields, no side reactions such as bromination either at the anomeric position or double bond, and even oxidation at the sulfur are some of the major advantages.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics