76334-65-1

Basic information

• Product Name: 5-(2,2-dimethoxy-1-methylethyl)-2'-deoxyuridine
• Synonyms: 5-(2,2-dimethoxy-1-methylethyl)-2'-deoxyuridine
• CAS NO: 76334-65-1
• Molecular Weight: 330.338
• Mol File: 76334-65-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-(2,2-dimethoxy-1-methylethyl)-2'-deoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2,2-dimethoxy-1-methylethyl)-2'-deoxyuridine(76334-65-1)
• EPA Substance Registry System: 5-(2,2-dimethoxy-1-methylethyl)-2'-deoxyuridine(76334-65-1)

Safety Data

• Hazardous Substances Data: 76334-65-1(Hazardous Substances Data)

Upstream product

• 557-31-3 3-ethoxyprop-1-ene 
• 65505-76-2 C⁵-chloromercuri-2'-deoxyuridine 
• 67-56-1 methanol 

Relevant articles and documents

C-5-Substituted Pyrimidine Nucleosides. 3. Reaction of Allylic Chlorides, Alcohols, and Acetates with Pyrimidine Nucleoside Derived Organopalladium Intermediates

The reaction of allylic chlorides with pyrimidine nucleoside derived organopalladium intermediates was investigated.The organopalladium intermediates were generated in situ by the reaction of 5-(chloromercuri)-2'-deoxyuridine (1), 5-(chloromercuri)cytidine, and 5-(chloromercuri)-2'-deoxycytidine with a catalytic amount of Li2PdCl4 in methanol.With allyl chloride, 1 gives principally 5-allyl-2'-deoxyuridine, some of which reacts further with 1 to give the cross-linked nucleosides (E)-5--2'-deoxyuridine (5) and5--2'-deoxyuridine (6). 3-Chloro-1-butene couples with 1 to give mainly (E)-5-(2-buten-1-yl)-2'-deoxyuridine (9) and lesser amounts of the Z isomer 10 and 5-(1-methyl-2-propen-1-yl)-2'-deoxyuridine (11).Nucleoside 11 appears to be the product of a coupling reaction between 1-methoxy-2-butene and the organopalladium intermediate derived from 1.Allylic chlorides are transformed to allyl methyl ethers in 0.1 M Li2PdCl4 at a slightly slower rate than the coupling reaction.Higher allylic chloride homologues show greater regioselectivity and stereoselectivity. 3-Chloro-1-pentene leads to (E)-5-(2-penten-1-yl)-2'-deoxyuridine (14) as the sole major product in 50percent yield.When a cyano group was attached to C-5 of 3-chloro-1-pentene, the resultant allylic chloride coupled regioselectivity but gave both cis and trans isomers.The mechanism of the coupling reaction is discussed and a basis for stereoselectivity proposed.Allylic alcohols and acetates couple more slowly and less cleanly, leading to lower yields of the same allylic-substituted pyrimidine nucleosides obtained with allylic chlorides.In some instances other products could be isolated.Nucleoside 1 and 3-hydroxy-4-methyl-1-pentene gave 5-(4-methyl-2-penten-1-yl)-2'-deoxyuridine (16) as well as 5-(4-methyl-3-oxopentyl)-2'-deoxyuridine (20). 3-Acetoxy-4-methyl-1-pentene led to (E)-5-(4-methyl-1,3-pentadien-1-yl)-2'-deoxyuridine (23).Mechanisms leading to these products are discussed.