845620-48-6

Basic information

• Product Name: Cytidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-5-iodo-
• CAS NO: 845620-48-6
• Molecular Formula: C30H30IN3O6
• Molecular Weight: 655.489
• Mol File: 845620-48-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Cytidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-5-iodo-(CAS DataBase Reference)
• NIST Chemistry Reference: Cytidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-5-iodo-(845620-48-6)
• EPA Substance Registry System: Cytidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-5-iodo-(845620-48-6)

Safety Data

• Hazardous Substances Data: 845620-48-6(Hazardous Substances Data)

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 611-53-0 5-Iodo-2'-deoxycytidine 

Downstream Products

• 1472616-91-3 N⁴-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-iodocytosine 
• 1472616-92-4 N⁴-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythropentofuranosyl]-5-(triisopropylsilylethynyl)cytosine 
• 1472616-93-5 N⁴-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythropentofuranosyl]-5-(triisopropylsilylethynyl)cytosine 3′-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 
• 669776-74-3 3'-O,4-N-diacetyl-5'-O-4,4'-dimethoxytrityl-5-(3''-trifluoroacetamidobutynyl)-2'-deoxycytidine 
• 669776-76-5 3'-O-acetyl-5'-O-4,4'-dimethoxytrityl-5-(3''-trifluoroacetamidobutynyl)-2'-deoxycytidine 
• 669776-73-2 4-[3'-O,4-N-diacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidin-5-yl]but-3-ynyl tert-butyl disulfide 
• 669776-75-4 4-[3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidin-5-yl]but-3-ynyl tert-butyl disulfide 
• 647852-37-7 4-[5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidin-5-yl]but-3-ynyl tert-butyl disulfide 
• 669776-72-1 5'-O-4,4'-dimethoxytrityl-5-(3''-trifluoroacetamidobutynyl)-2'-deoxycytidine 
• 669776-71-0 5'-O-4,4'-dimethoxytrityl-5-(4-benzoylthio-1-butynyl)-2'-deoxycytidine 

Relevant articles and documents

Functionalized Silver-Ion-Mediated α-dC/β-dC Hybrid Base Pairs with Exceptional Stability: α-d-5-Iodo-2′-Deoxycytidine and Its Octadiynyl Derivative in Metal DNA

Silver-mediated α-dC–Ag+–β-dC hybrid base pairs decorated with 5-iodo- or 5-octadiynyl residues are well accommodated in duplex DNA. A strong Tm increase and favorable thermodynamic data for duplex DNA were observed after addition of silver ions. The phenomenon is particularly obvious when both nucleobases of the base pairs are functionalized. Neither the position of the base pair, nor the type of 5-substituent had a negative influence. On the contrary, functionalization of conventional silver-mediated β-dC–Ag+–β-dC homo base pairs showed a negative impact induced by the bulky substituents. To this end, cytosine modified 12-mer oligodeoxynucleotides were prepared by solid-phase synthesis employing new α-anomeric 2′-deoxycytidine phosphoramidites. A multigram scale synthesis was developed for 5-iodo-α-d-2′-deoxycytidine (1) employing the direct glycosylation of cytosine with Hoffer's α-d-halogenose followed by separation of anomeric DMT nucleosides. Regarding base-pair stability and functionalization silver-mediated α/β-dC hybrid base pairs were found to be superior to β/β-dC homo pairs. According to their extraordinary properties, they might find applications in DNA diagnostics, material science, or nanotechnology.

Triisopropylsilyl modified deoxycytidine phosphoramidite monomer and preparation method and application thereof

The invention discloses a triisopropylsilyl modified deoxycytidine phosphoramidite monomer and a preparation method and application thereof. The chemical structural formula of the triisopropylsilyl modified deoxycytidine phosphoramidite monomer is shown in the formula I (see the description), wherein DMTr- is 4, 4'-dimethoxy trityl, and N(i-Pr)2- is N, N-diisopropyl amino. The preparation method comprises the following steps of: protecting a 5'-end group in 5-I-deoxycytidine, protecting amino of the 5-I-deoxycytidine, introducing triisopropylsilyl into a No. 5 site of a base for modification,and introducing the deoxycytidine into phosphoramidite to obtain the triisopropylsilyl modified deoxycytidine phosphoramidite monomer. The triisopropylsilyl modified deoxycytidine phosphoramidite monomer shown in the formula I is applied to the preparation of oligonucleotide. The oligonucleotide can be prepared from the triisopropylsilyl modified deoxycytidine phosphoramidite monomer shown in theformula I by a DNA solid-phase synthesis method. The preparation method is simple, and can be used for preparing steady-state and transient-state infrared spectrum structure probes.

2'-deoxycytidines carrying amino and thiol functionality: synthesis and incorporation by Vent (exo-) polymerase.

[reaction: see text] The synthesis of 2'-deoxycytidine nucleosides bearing amino and thiol groups appended to the 5-position of the nucleobase via a butynyl linker is described. The corresponding triphosphates were then synthesized from the nucleoside and incorporated into oligonucleotides by Vent (exo(-)) DNA polymerase. The ability of Vent (exo(-)) polymerase to amplify oligonucleotides containing these functionalized cytidine derivatives in a polymerase chain reaction (PCR) was demonstrated for the amino-functionalized derivative.