67441-18-3

Upstream product

• 106-96-7 propargyl bromide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 492-62-6 alpha-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 142435-23-2 (1R,2R,3S,4R,5R)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-propenyloxy-tetrahydro-furo[2,3-d][1,3]dioxole 
• 142363-22-2 1,2:5,6-di-O-isopropylidene-3-O-(allenyl)-α-D-glucofuranoside 
• 20316-77-2 (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole 
• 582-52-5 1,2:5,6-diacetone-D-glucose 

Downstream Products

• 835613-49-5 (3aR,4S,5R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4R-yl)-2,2-dimethyl-6-(3-phenylprop-2-ynyloxy)-tetrahydrofuro[2,3-d][1,3]dioxole 
• 835613-40-6 (5aS,5bR,8aR,9aR)-7,7-dimethyl-2-phenyl-2,4,5a,5b,8a,9a-hexahydro-5,6,8,9-tetraoxa-1,2-diaza-cyclopenta[b]-as-indacene 
• 142363-26-6 (S)-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-methylene-3-phenyl-5,6-dihydro-4H-[1,2]oxazine 
• 142363-27-7 (S)-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-5-methyl-3-phenyl-6H-[1,2]oxazine 
• 1005198-76-4 C₂₂H₂₇NO₇ 
• 1005198-77-5 C₂₃H₂₉NO₈ 
• 1005198-78-6 C₂₄H₃₁NO₉ 
• 1315509-69-3 C₃₀H₃₇N₅O₇ 
• 1403989-92-3 5-(2-bromobenzyloxymethyl)-2,2-dimethyl-6-prop-2-ynyloxytetrahydrofuro[2,3-d][1,3]dioxole 

Relevant academic research and scientific papers

Synthesis of enantiopure 1-alkoxyallenes and their 3-alkylated derivatives

A series of enantiopure 1-alkoxyallenes 1a-1f was prepared starting from propargyl bromide and the corresponding optically active alcohols via propargyl ethers 3a-3f as intermediates. In addition, disubstituted enantiopure allene derivatives 5a-5c were synthesized by isomerization of the corresponding alkynes 4a-4c. Allene derivative 5a was also prepared via an alternative route with 1-trimethylsilylallene derivative 6a as crucial intermediate.

Synthesis and in vitro evaluation of boronated uridine and glucose derivatives for boron neutron capture therapy

The following boron-containing nucleoside and glucose derivatives have been synthesized as potential boron delivery agents for boron neutron capture therapy (BNCT): 2'-O(o-carboran-1-ylmethyl)uridine (4a), 3'-O-(o-carboran-1- ylmethyl)uridine (4b), sodium 7-(uridin-2'-ylmethyl)dodecahydro-7,8-dicarba- nido-undecaborate (5), 5'-O-(o-carboran-1-ylmethyl)uridine (9), and 3'-O-(o- carboran-1-ylmethyl)-D-glucose (13). In vitro cellular uptake studies were performed with F98 rat glioma cells. Following 16 h incubation, cellular boron concentrations were determined by direct current plasma atomic emission spectroscopy (DCP-AES). Boron concentrations ranged from 65 to 103 μg/g of cells for the neutral closo structures compared with 1.5 μg/g of cells for the charged nido species. Cellular uptake of sodium mercaptoundecahydro- closo-dodecaborate (BSH), the compound currently being used in Japan for the treatment of malignant brain tumors by BNCT, was 2 μg/g of cells.

Synthesis of enantiopure pyranoisoxazole and oxepanoisoxazole derivatives from O-alkynyl carbohydrate ethers by the application of intramolecular nitrile oxide cycloaddition

A useful synthesis of enantiomerically pure pyrano- and oxepanoisoxazole derivatives by the application of intramolecular cycloaddition of 3-O-alkynyl carbohydrate nitrile oxides is described. One of the isoxazole derivatives was transformed to a furylpyran system having the lasalocid A skeleton using 2-O-allyl carbohydrate nitrone cycloaddition.

An efficient synthesis of enantiopure 1-alkoxy-1,2-propadienes from propargyl bromide

A number of enantiopure functionalized alcohols have been O-allenylated by reaction of their corresponding sodium alcoholates with propargyl bromide followed by t-BuOK catalyzed isomerization of the resulting propargyl ethers, in good overall yields.

Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates

Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har

Synthesis of Triazole-Containing Furanosyl Nucleoside Analogues and Their Phosphate, Phosphoramidate or Phoshonate Derivatives as Potential Sugar Diphosphate or Nucleotide Mimetics

The synthesis of stable and potentially bioactive xylofuranosyl nucleoside analogues and potential sugar diphosphate or nucleotide mimetics comprising a 1,2,3-triazole moiety is reported. 3′-O-Methyl-branched N-benzyltriazole isonucleosides were accessed

Mitigation of Hydrophobicity-Induced Immunotoxicity by Sugar Poly(orthoesters)

Polymeric nanoparticles (NPs) derived from self-assemblies of amphiphilic polymers have demonstrated great potential in clinical applications. However, there are challenges ahead. Notably, immunotoxicity remains a major roadblock that deters the NPs from

Metal- and Phenol-Free Synthesis of Biaryl Ethers: Access to Dibenzobistriazolo-1,4,7-oxadiazonines and Vancomycin-Like Glyco-Macrocycles as Antibacterial Agents

An efficient synthesis of biaryl ethers, from electron-deficient aryl halides using NaH/DMSO under metal- and phenol-free conditions, has been achieved to access dibenzo-bistriazolo-1,4,7-oxadiazonines and vancomycin-like glyco-macrocycles. A 44-membered glyco-macrocycle showed promising activity against vancomycin-resistant Staphylococcus aureus (VRSA).

Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization

A series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylidene or oxazoline protected sugar derivatives.The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation.The oxazoline protected D-GlcNAc derivative gave either pyranose or furanose derivatives on glycosidation depending on the amount of Lewis acid used.The diversely functionalized glycoconjugates with azide or alkyne groups are potentially useful for the synthesis of multifunctionalized complex glycoconjugates via click reactions.

An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks

An efficient, eco-compatible diversity-oriented synthesis (DOS) approach for the generation of library of sugar embedded macrocyclic compounds with various ring size containing 1,2,3-triazole has been developed. This concise strategy involves the iterative use of readily available sugar-derived alkyne/azide-alkene building blocks coupled through copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction followed by pairing of the linear cyclo-adduct using greener reaction conditions. The eco-compatibility, mild reaction conditions, greener solvents, easy purification and avoidance of hazards and toxic solvents are advantages of this protocol to access this important structural class. The diversity of the macrocycles synthesized (in total we have synthesized 13 macrocycles) using a set of standard reaction protocols demonstrate the potential of the new eco-compatible approach for the macrocyclic library generation.