156592-85-7

Upstream product

• 96253-10-0 1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione 
• 6258-60-2 p-methoxybenzylmercaptan 
• 76-83-5 trityl chloride 
• 6554-10-5 5'-O-trityluridine 
• 110524-37-3 1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione 
• 58-96-8 uridine 

Downstream Products

• 299177-12-1 3'-deoxy-3'-(2,4-dinitrophenyldisulfanyl)uridine 
• 175025-56-6 3'-S-(2,4-dinitrophenylsulfanyl)-2'5'-bis-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl]-3'-thiouridine 
• 175025-55-5 3'-S-(4-methoxybenzyl)-3'-thiouridine 

Relevant academic research and scientific papers

Preparation and cleavage reactions of 3′-thiouridylyl-(3′→5′)-uridine

3′-Thiouridylyl-(3′→5′)-uridine [(Us)pU] 3 is prepared by coupling together the disulfide 14 and the 5′-H-phosphonate 18, and then removing the protecting groups. (Us)pU 3 readily undergoes cleavage in 0.05 mol dm-3 sodium glycinate buffer (pH 10.06) at 50 °C to give, in the first instance, uridine 4 and 3′-thiouridine 2′,3′-cyclic phosphorothioate 21; in glacial acetic acid at 30 °C, it rapidly undergoes cleavage in essentially the same way. The behaviour of (Us)pU 3 is compared with that of uridylyl-(3′→5′)-uridine (UPU) 1a under the same basic and acidic reaction conditions. (Us)pU 3 and 3′-thiouridine 2′,3′-cyclic phosphorothioate 21 are both substrates for ribonuclease A; (Us)pU 3 is a substrate for Crotalus adamanteus snake venom phosphodiesterase but not for calf spleen phosphodiesterase.

Synthesis of 2',3'-Dithiouridine

The synthesis of 2',3'-dithiouridine 2, starting from uridine, is described.