68115-75-3

Upstream product

• 22169-71-7 (R)-1-((3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol 
• 98-88-4 benzoyl chloride 
• 13964-23-3 3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose 
• 2595-05-3 Diacetone D-glucose 
• 208525-43-3 1,2:5,6-di-O-isopropylidene-3-O-(N-imidazole-1-sulfonyl)-α-D-allofuranose 

Downstream Products

• 143419-07-2 3-azido-6-O-benzoyl-3-deoxy-1,2-O-isopropylidene-α-D-glucopyranose 
• 143418-94-4 C₂₂H₂₀BrN₃O₇ 
• 143419-11-8 C₃₁H₃₆N₄O₁₃ 
• 143418-96-6 C₃₉H₄₄N₄O₁₄ 

Relevant academic research and scientific papers

Synthetic studies on 2'-substituted-4'-thiocytidine derivatives as antineoplastic agents

As potential antineoplastic agents, we have synthesized 4'-thioFAC and 4'-thiocytarazid by developing an alternative synthetic method. 4'-ThioFAC showed potent antineoplastic activities in vivo as well as in vitro.

An Alternative Synthesis of the Antineoplastic Nucleoside 4′-ThioFAC and Its Application to the Synthesis of 4′-ThioFAG and 4′-Thiocytarazid

Previously, we synthesized 4′-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method for the synthesis of 4′-thionucleosides. In the original synthesis, carbons from C1 to C5 of D-glucose were used. The new method also starts from D-glucose but uses carbons closer to the tail (C2-C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the 1-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a β-anomer of 4′-thioFAC. The reaction of 2,6-diaminopurine with the 1-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a β-anomer of 4′-thioFAG, a guanine congener of 4′-thioFAC, selectively. Using a similar approach, we synthesized 4′-thiocytarazid, which was not possible using the original method.

2-Substituted arabinofuranosyl nucleosides and nucleotides

Novel arabinofuranosyl nucleosides and nucleotides having 2'-azido, 2'-amino, or 2'-hydrocarbylamino substituents, which have antitumor, antiviral, and antimicrobial properties, are prepared by condensation of a pyrimidine, purine, or 1,3-oxazine base wit