134111-33-4

Upstream product

• 1017605-11-6 1-[2-deoxy-3,5-di-O-acetyl-4-thio-β-D-ribofuranosyl]thymine 
• 1044749-36-1 5-tributylstannyl-4'-thio-2′-deoxyuridine 
• 74-88-4 methyl iodide 
• 169736-17-8 1-O-acetyl-2-deoxy-4-thio-3,5-di-O-p-toluoyl-4-thio-D-erythro-pentofuranose 
• 148504-79-4 5'-O-acetyl-3'-O-(tert-butyldimethylsilyl)-4-thiothymidine 
• 148556-03-0 5-O-acetyl-3-O-tert-butyldimethylsilyl-2-deoxy-4-thio-D-erythro-pentofuranoside 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 869347-07-9 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine 
• 869347-11-5 1-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine 
• 869347-10-4 1-[2-O,2'-anhydro-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine 
• 869347-08-0 1-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine 
• 160452-63-1 5'-O-acetyl-4'-thiothymidine 
• 148504-80-7 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-tetrahydro-thiophen-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 134700-16-6 3',5'-di-O-benzyl-4'-thiothymidine 

Downstream Products

• 65-71-4 thymin 
• 137719-41-6 3'-azido-3'-deoxy-4'-thio-5'-O-tritylthymidine 
• 139031-43-9 5'-O-trityl-4'-thio-2,3'-anhydrothymidine 
• 154821-09-7 1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-1,1-dioxo-tetrahydro-1λ⁶-thiophen-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 137719-39-2 5'-O-trityl-4'-thiothymidine 
• 151607-33-9 1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-thiophen-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Highly efficient syntheses of [methyl-11C]thymidine and its analogue 4′-[methyl-11C]thiothymidine as nucleoside PET probes for cancer cell proliferation by Pd0-mediated rapid C-[ 11C]methylation

Pd0-mediated rapid couplings of CH3I (and then [ 11C]CH3I) with excess 5-tributylstannyl-2′- deoxyuridine and -4′-thio-2′-deoxyuridine were investigated for the syntheses of [methyl-11C]thymidine and its stable analogue, 4′-[methyl-11C]thiothymidine as PET probes for cancer diagnosis. The previously reported conditions were attempted using Pd 2(dba)3/P(o-CH3C6H4) 3 (1:4 in molar ratio) at 130°C for 5 min in DMF, giving desired products only in 32 and 30% yields. Therefore, we adapted the current reaction conditions developed in our laboratory for heteroaromatic compounds. The reaction using CH3I/stannane/Pd2(dba)3/P(o- CH3C6H4)3/CuCl/K2CO 3 (1:25:1:32:2:5) at 80°C gave thymidine in 85% yield. Whereas, CH3I/stannane/Pd2(dba)3/P(o-CH 3C6H4)3/CuBr/CsF (1:25:1:32:2:5) including another CuBr/CsF system promoted the reaction at a milder temperature (60°C), giving thymidine in 100% yield. Chemo-response of thiothymidine-precursor was different from thymidine system. Thus, the above optimized conditions including CuBr/CsF system gave 4′-thiothymidine only in 40% yield. The reaction using 5-fold amount of CuBr/CsF at 80°C gave much higher yield (83%), but unexpectedly, the reaction was accompanied by a considerable amount of undesired destannylated product. Such destannylation was greatly suppressed by changing to a CuCl/K2CO3 system using CH3I/stannane/Pd2(dba)3/P(o-CH 3C6H4)3/CuCl/K2CO 3 (1:25:1:32:2:5) at 80°C, giving the 4′-thiothymidine in 98% yield. The each optimized conditions were successfully applied to the syntheses of the corresponding PET probes in 87 and 93% HPLC analytical yields. [11C]Compounds were isolated by preparative HPLC after the reaction conducted under slightly improved conditions, exhibiting sufficient radioactivity of 3.7-3.8 GBq and specific radioactivity of 89-200 GBq mol -1 with radiochemical purity of ≥99.5% for animal and human PET studies.

Synthesis and X-Ray Structure of 4'-Thiothymidine

4'-Thiothymidine was synthesized by SnCl4 mediated coupling of 5-O-acetyl-3-O-tert-butyldimethylsilyl-2-deoxy-4-thio-D-erythro-pentofuranoside with 2,4-bis(trimethylsilyl)thymine and the structure was determined by X-ray analysis.

Synthesis and anti-HIV activity of 4′-substituted 4′-thiothymidines: A new entry based on nucleophilic substitution of the 4′-acetoxy group

Diacetoxylation of 1-(2,5-dideoxy-β-L-glycero-pent-4-eno-4- thiofuranosyl)thymine (13) with Pb(OAc)4 allowed introduction of an acetoxy leaving group to the 4′-position. Nucleophilic substitution of the resulting 4′-acetoxy derivative (14) with

Practical synthesis of 2′-deoxy-4′-thioribonucleosides: Substrates for the synthesis of 4′-thioDNA

We report herein a practical synthesis of 4′-thiothymidine (15) and appropriately protected 2′-deoxy-4′-thiocytidine (16), -thioadenosine (27), and -thioguanosine (29) derivatives, substrates for the synthesis of 4′-thioDNA, from the corresponding 4′- thi

2'-deoxy-4'-thioribonucleosides and their antiviral activity

2'-Deoxy-4'-thio-ribonucleosides, intermediates in their production, and their use as antiviral and anticancer agents are disclosed.

Some reactions of 4′-thionucleosides and their sulfones

We report interesting and novel reactions of 4′-thionucleosides and their sulfone derivatives when a good leaving group is present in the 5′-position. The results have important implications for the phosphorylation of these nucleoside analogues by standard chemical procedures. Possible mechanisms for these reactions are discussed.

The synthesis and biological activity of certain 4'-thionucleosides

Results are presented on the synthesis and biological activity of several types of 4'-thionucleosides as potential anticancer agents. Detailed studies on the mechanism of action of 4'-thiothymidine are also presented.

Syntheses and antitumor activities of D- and L-2'-deoxy-4'-thio pyrimidine nucleosides

Both enantiomers of 2'-deoxy-4'-thiouridine (9) and 15, 4'-thiothymidine (10) and 16, and 2'-deoxy-4'-thiocytidine (14) and 17 and 1-(2-deoxy-4-thio- β-D-erythro-pentafuranosyl)-5-trifluoromethyluracil (11) were synthesized. The key coupling reactions were performed by the reaction of D- or L- enantiomers of ethyl 5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4- thio-α,β-xylofuranoside (1) or 18 and 2,4-bis(trimethylsilyloxy)pyrimidine in the presence of SnCl4 in acetonitrile. Cytotoxicities against L-1210 and KB-cells for the compounds 9, 10, 11, 14, 15, 16, and 17 were examined. The compounds 10 and 11 were potentially active.

Synthesis and Biological Activity of 2'-Deoxy-4'-thio Pyrimidine Nucleosides

2'-Deoxy-4'-thiocytidine (7β), 2'-deoxy-4'-thiouridine (9), and 4'-thiothymidine (10) have been synthesized and evaluated for cytotoxicity in vitro.All these compounds were cytotoxic to L1210, H-Ep-2, and CCRF-CEM cell lines. 4'-Thiothymidine was also act

The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues

Starting from benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside (4), the following 2'-deoxy nucleoside analogues have been synthesized: 4'-thiothymidine (8), 3'-azido-4'-thio-deoxythymidine (10), and (E)-5-(2-bromovinyl)-4'-thio-2'-deoxy