102212-98-6 Usage
Uses
5'-O-DMT-N4-Benzoyl-2'-deoxycytidine 3'-CE phosphoramidite is used to prepare antisense oligonucleotides containing conformationally constrained methoxyaminomethylene and aminooxymethylene and aminomethylene bridged nucleoside analogs.
Synthesis
These Examples illustrate the phosphitylation of several protected nucleoside reagents with 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite in the presence of several activators according to the present invention. Eleven phosphitylation reactions (1-11) comprising reacting a protected nucleoside reagent with 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite in the presence of an acid-base activator according to the present invention were conducted, and the product yields of each calculated, as described in the General Procedure, below. The various combinations of protected nucleoside, activator base, activator acid, solvent, and yield for each of the 11 reactions are listed in Table 1. General Procedure: The activator base (1.1 to 1.2 equivalents) is added to the solvent and 0.95 to 1.1 equivalents of activator acid is subsequently added thereto at ambient temperature to form the activator solution. About 1 equivalent of the protected nucleoside is dissolved in about 10 equivalents of the solvent in a separate vessel and about 3 equivalents of the solvent is then distilled off under reduced pressure. About 1 to 1.2 equivalents of 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite is added to the nucleoside mixture at ambient temperature, and the activator solution prepared previously is then added to the nucleoside mixture at ambient temperature with vigorous stirring. After 12 hours, the reaction mixture is diluted with toluene and washed with water. The organic layer is separated, dried over sodium sulfate if necessary, and concentrated under reduced pressure. The yield of the desired amidite is then calculated using HPLC techniques, that is, the resulting product mixture is run through an HPLC column using an appropriate eluent, and the area under the HPLC peaks used to determine the %yield of product in the mixture.
Check Digit Verification of cas no
The CAS Registry Mumber 102212-98-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,2,2,1 and 2 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 102212-98:
(8*1)+(7*0)+(6*2)+(5*2)+(4*1)+(3*2)+(2*9)+(1*8)=66
66 % 10 = 6
So 102212-98-6 is a valid CAS Registry Number.
102212-98-6Relevant articles and documents
A novel phosphitylating reagent for in situ generation of deoxyribonucleoside phosphoramidites
Zhang, Zhaoda,Tang, Jin Yan
, p. 331 - 334 (1996)
A new phosphitylating reagent, 2-cyanoethoxy(N,N-diisopropylamino)3-nitro-1,2,4-triazolylphosphine (1), has been prepared and effectively used in in situ generation of 5'-DMT-nucleoside phosphoramidites and automated syntheses of oligonucleotides.
Microwave-assisted preparation of nucleoside-phosphoramidites
Meher,Efthymiou,Stoop,Krishnamurthy
supporting information, p. 7463 - 7465 (2014/07/07)
Microwave-assisted phosphitylation of sterically hindered nucleosides is demonstrated to be an efficient method for the preparation of corresponding phosphoramidites (otherwise onerous under standard conditions) and is shown to be general in its applicability. the Partner Organisations 2014.
Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry
Hardacre, Christopher,Huang, Haifeng,James, Stuart L.,Migaud, Marie E.,Norman, Sarah E.,Pitner, William R.
, p. 5846 - 5848 (2011/06/26)
Ionic liquids have been used in combination with ball milling on a range of chlorophosphoramidite reagents to phosphitylate nucleosides and 2-deoxynucleosides. The enhanced stability offered by the ionic liquid mediated processes combined with efficient mass transfer induced by ball milling has enabled excellent yields to be obtained even when using small dialkyl amino groups as well as the more commonly used diisopropylamino protection.