87818-00-6

Basic information

• Product Name: 2',3'-O-isopropylidene-5'-O-methoxymethyl-5-methyl-6-phenylthiouridine
• Synonyms: 2',3'-O-isopropylidene-5'-O-methoxymethyl-5-methyl-6-phenylthiouridine
• CAS NO: 87818-00-6
• Molecular Weight: 450.513
• Mol File: 87818-00-6.mol

Chemical Properties

• CAS DataBase Reference: 2',3'-O-isopropylidene-5'-O-methoxymethyl-5-methyl-6-phenylthiouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-O-isopropylidene-5'-O-methoxymethyl-5-methyl-6-phenylthiouridine(87818-00-6)
• EPA Substance Registry System: 2',3'-O-isopropylidene-5'-O-methoxymethyl-5-methyl-6-phenylthiouridine(87818-00-6)

Safety Data

• Hazardous Substances Data: 87818-00-6(Hazardous Substances Data)

Upstream product

• 2073-43-0 2',3'-O,O-isopropylidene-5-methyluridine 
• 87817-95-6 2',3'-O-isopropylidene-5'-O-methoxymethyl-5-methyluridine 
• 882-33-7 diphenyldisulfane 
• 80614-90-0 2',3'-O-isopropylidene-5'-O-methoxy-methyl-6-phenylthiouridine 
• 74-88-4 methyl iodide 

Downstream Products

• 1463-10-1 5-Methyluridine 
• 87818-13-1 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-6-phenylsulfanyl-1H-pyrimidine-2,4-dione 

Relevant articles and documents

SYNTHETIC ROUTE TO 5-SUBSTITUTED URIDINES VIA A NEW TYPE OF DESULFURIZATIVE STANNYLATION

Phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidine.Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives.The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis.The whole sequence constitutes a new route to 5-substituted uridines.Application of this method to 2'-deoxyuridine is also described.

DESULFURIZATIVE STANNYLATION OF URACIL DERIVATIVES

Phenylthio group in the C-6 or C- position of uracil moiety can be removed by radical mediated stannylation with tributyltin hydride followed by protonolysis, providing a new route to 5-substituted uridines.

Synthesis and biological activities of 5-substituted 6-phenylthio and 6-iodouridines, a new class of antileukemic nucleosides

A new class of 5,6-disubstituted uridines, in which the C-6 position was occupied by phenylthio group or iodine, were synthesized via lithiation of the corresponding 5-substituted 2',3'-O-isopropylidene-5'-O-methoxymethyl-uridines and subsequent electroph