16750-07-5

Upstream product

• 154-17-6 D-2-deoxyglucose 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 563-63-3 silver(I) acetate 
• 2873-29-2 D-glucal triacetate 
• 2946-11-4 1,3,4,6-Tetra-O-acetyl-2-bromo-2-deoxy-β-D-glucopyranose 
• 69908-91-4 5,5-dimethyl-tioxo-2-(3,4,6-tri-O-acetyl-2-deoxy-α-Darabino-hexopyranosylthio)-1,3,2-dioxaphosohorinane 
• 64-19-7 acetic acid 
• 76695-54-0 1,3,4,6-tetra-O-acetyl-2-deoxy-2-isocyano-β-D-glucose 
• 13242-53-0 acetobromomannose 
• 61-58-5 2-deoxy-D-arabino-hexopyranose 
• 13299-16-6 β-D-2-deoxy-glucopyranose 
• 74638-66-7 2-deoxy-2-iodo-1,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 17460-45-6 tetra-acetyl glucosamine 

Relevant academic research and scientific papers

Practical synthesis of 2-deoxy sugars via metal free deiodination reactions

2-Deoxy-glycosides, in which the C-2 hydroxyl group is replaced with a hydrogen atom, are important motifs in numerous bioactive natural products and pharmaceutical molecules. Herein, an improved dilauroyl peroxide-mediated radical deiodination reaction b

INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF

Provided are molecules capable of binding to binding pockets of Plasmodium falciparum hexose transporter (PfHT) or analogs thereof and complexes comprising the same. Also provided herein are inhibitors of PfHT, pharmaceutical compositions comprising the i

Direct Deamination of Primary Amines via Isodiazene Intermediates

We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.

Synthesis method of ginseng saponin new derivative, product produced by synthesis method and application of ginseng saponin new derivative

The invention relates to a synthesis method of a ginseng saponin new derivative, a product produced by the synthesis method and application of the ginseng saponin new derivative and belongs to the technical field of medicines. The ginseng saponin new derivative is obtained by taking existing ginseng saponin as a raw material and reacting with 2-deoxy-D-glucose; the ginseng saponin new derivative is a medical composition of an active ingredient and can be used as a drug preparation of a crude drug; the ginseng saponin new derivative provided by the invention has relatively strong anti-cancer activity and can be used for preparing drugs for resisting stomach cancer, colon cancer, lung cancer and liver cancer; the ginseng saponin new derivative can be combined with antibacterial drugs including ofloxacin, clindamycin and the like, and has the effects of enhancing the sterilization effect and shortening a disease period; the ginseng saponin new derivative can also be combined with myocardium protection drugs including creatine phosphate sodium, cyclic adenosine monophosphate and the like, so that a myocardium protection effect is enhanced; to sum up, the ginseng saponin new derivative has a very wide application value.

Organoboron-catalyzed regio- and stereoselective formation of β-2-deoxyglycosidic linkages

A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-sel

NaBH3CN and other systems as substitutes of tin and silicon hydrides in the light or heat-initiated reduction of halosugars: A tunable access to either 2-deoxy sugars or 1,5-anhydro-itols

UV light-promoted reduction of acetobromoglucose by NaBH3CN in t-BuOH afforded 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose in high yield and purity, via a Surzur-Tanner rearrangement, while, with 10 mol % thiophenol added, acetylated 1,5-anhydro-d-glucitol was cleanly obtained. Such tin-free and mild reductions, presumed to proceed via radical pathways, were more efficient with NaBH3CN compared to NaBH4 or NaBD 4, and do not occur with acetochloroglucose. Similar reductions to 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose were achieved upon heating to 80 C t-BuOH or CH3CN solutions of NaBH3CN and AIBN, but with a lower selectivity due to competing ionic reactions. With other pyranosyl bromides, reductions by NaBH3CN could be tuned similarly (d-galacto), but some (d-manno, 5-thio-d-xylo) gave mainly or exclusively 1,5-anhydro-itols. Other conditions, or reagents promoting SET process, afforded also reduced products, but with lower rates or selectivities. Primary iodides were reduced readily with NaBH3CN under UV light.

Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol

A mild, stereoselective, and quick approach to accessing alkynyl and alkenyl C-glycosides via BF3?Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

DABCO: An efficient promoter for the acetylation of carbohydrates and other substances under solvent-free conditions

A simple, mild and efficient solvent-free method for the acetylation of carbohydrates, and their partially protected derivatives, as well as non-carbohydrate substances in excellent yields in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is described with the advantage of tolerance to various functional groups, short reaction time and ease of product isolation.

Erosion of stereochemical control with increasing nucleophilicity: O-glycosylation at the diffusion limit

(Chemical Equation Presented) Nucleophilic substitution reactions of 2-deoxyglycosyl donors indicated that the reactivity of the oxygen nucleophile has a significant impact on stereoselectivity. Employing ethanol as the nucleophile resulted in a 1:1 (α:β) ratio of diastereomers under SN1-like reaction conditions. Stereoselective formation of the 2-deoxy-α-O-glycoside was only observed when weaker nucleophiles, such as trifluoroethanol, were employed. The lack of stereoselectivity observed in reactions of common oxygen nucleophiles can be attributed to reaction rates of the stereochemistry-determining step that approach the diffusion limit. In this scenario, both faces of the prochiral oxocarbenium ion are subject to nucleophilic addition to afford a statistical mixture of diastereomeric products. Control experiments confirmed that all nucleophilic substitution reactions were performed under kinetic control.