70284-47-8

Basic information

• Product Name: 4-3''-O-DIACETYL-2''DEOXYCYTIDINE
• Synonyms: 4-3''-O-DIACETYL-2''DEOXYCYTIDINE;N(sup 4)-3'-O-diacetyl-2'-deoxycytidine;N4,3′-O-Diacetyl-2′-deoxycytidine;N-Acetyl-2'-deoxycytidine 3'-acetate;N4-Acetyl-3'-O-acetyl-2'-deoxycytidine
• CAS NO: 70284-47-8
• Molecular Formula: C₁₃H₁₇N₃O₆
• Molecular Weight: 311.29058
• Mol File: 70284-47-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: ?20°C
• CAS DataBase Reference: 4-3''-O-DIACETYL-2''DEOXYCYTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-3''-O-DIACETYL-2''DEOXYCYTIDINE(70284-47-8)
• EPA Substance Registry System: 4-3''-O-DIACETYL-2''DEOXYCYTIDINE(70284-47-8)

Safety Data

• Hazardous Substances Data: 70284-47-8(Hazardous Substances Data)

Upstream product

• 70284-43-4 N⁴,O^3'-diacetyl-O^5'-trityl-2'-deoxy-cytidine 
• 32909-05-0 N⁴-acetyl-2'-deoxycytidine 

Downstream Products

• 27999-55-9 O^5'-(toluene-4-sulfonyl)-2'-deoxy-cytidine 
• 1032-65-1 cytidine 5'-(dihydrogen phosphate) 

Relevant articles and documents

Differential reactivity of carbohydrate hydroxyls in glycosylations. II. The likely role of intramolecular hydrogen bonding on glycosylation reactions. Galactosylation of nucleoside 5'-hydroxyls for the syntheses of novel potential anticancer agents

Contrary to expectations, many primary hydroxy groups are completely unreactive in glycosylation reactions, or give the desired glycosides in very low yields accompanied by products of many side reactions. Hydrogens of such primary hydroxyls are shown to be intramolecularly hydrogen bonded. Intermediates formed by nucleophilic attack by these hydroxyls on activated glycosylating agents may resist hydrogen abstraction. This resistance to proton loss is postulated to be the origin of the observed unreactivity. It is shown that successful glycosylations take place under acidic conditions under which such hydrogen bonds cease to exist. Accordingly, direct galactosylations of the normally unreactive 5'-hydroxyls of nucleosides were accomplished for the first time with a galactose trichloroacetimidate donor in chloroform under silver triflate promotion. It is noted that such galactosylated anticancer nucleosides may have improved biological specificity. Contrary to expectations, many primary hydroxy groups are completely unreactive in glycosylation reactions, or give the desired glycosides in very low yields accompanied by products of many side reactions. Hydrogens of such primary hydroxyls are shown to be intramolecularly hydrogen bonded. Intermediates formed by nucleophilic attack by these hydroxyls on activated glycosylating agents may resist hydrogen abstraction. This resistance to proton loss is postulated to be the origin of the observed unreactivity. It is shown that successful glycosylations take place under acidic conditions under which such hydrogen bonds cease to exist. Accordingly, direct galactosylations of the normally unreactive 5′-hydroxyls of nucleosides were accomplished for the first time with a galactose trichloroacetimidate donor in chloroform under silver triflate promotion. It is noted that such galactosylated anticancer nucleosides may have improved biological specificity.