13233-20-0

Basic information

• Product Name: 2-thiocytidine
• CAS NO: 13233-20-0
• Molecular Weight: 259.286
• Mol File: 13233-20-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-thiocytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-thiocytidine(13233-20-0)
• EPA Substance Registry System: 2-thiocytidine(13233-20-0)

Safety Data

• Hazardous Substances Data: 13233-20-0(Hazardous Substances Data)

Upstream product

• 25030-30-2 4-methylsulfanyl-1-(β-D-ribofuranosyl)pyrimidine-2(1H)-thione 
• 627812-08-2 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methylsulfanyl-1,2-dihydropyrimidin-2-thione 

Downstream Products

• 156-81-0 2,4-diaminopyrimidine 
• 50574-59-9 cytidine 2′,3′-cyclic monophosphate 
• 65-46-3 CYTIDINE 
• 20235-78-3 2-thiouridine 
• 141-90-2 2-thiouracil 
• 333-49-3 2-thiocytosine 

Relevant articles and documents

A prebiotically plausible synthesis of pyrimidine β-ribonucleosides and their phosphate derivatives involving photoanomerization

Previous research has identified ribose aminooxazoline as a potential intermediate in the prebiotic synthesis of the pyrimidine nucleotides with remarkable properties. It crystallizes spontaneously from reaction mixtures, with an enhanced enantiomeric excess if initially enantioenriched, which suggests that reservoirs of this compound might have accumulated on the early Earth in an optically pure form. Ribose aminooxazoline can be converted efficiently into α-ribocytidine by way of 2,2'-anhydroribocytidine, although anomerization to β-ribocytidine by ultraviolet irradiation is extremely inefficient. Our previous work demonstrated the synthesis of pyrimidine β-ribonucleotides, but at the cost of ignoring ribose aminooxazoline, using arabinose aminooxazoline instead. Here we describe a long-sought route through ribose aminooxazoline to the pyrimidine β-ribonucleosides and their phosphate derivatives that involves an extraordinarily efficient photoanomerization of α-2-thioribocytidine. In addition to the canonical nucleosides, our synthesis accesses β-2-thioribouridine, a modified nucleoside found in transfer RNA that enables both faster and more-accurate nucleic acid template-copying chemistry.

Optical properties of thiopyrimidine nucleosides.

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Straightforward pyrimidine ring construction: A versatile tool for the synthesis of nucleobase and nucleoside analogues

A general route to 1,2,4-trisubstituted pyrimidines is described in one to three steps from a common key precursor, diazadienium iodide 2. An efficient preliminary [4+2] cyclocondensation reaction between the azabutadiene building block 2 and various iso(thio)cyanates constitutes an original construction of the pyrimidine skeleton. Subsequent structural modifications on the heterocycle allow the elaboration of a 1-substituted pyrimidine library that includes nucleoside analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.