Bz-rA Phosphoramidite
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Bz-rA Phosphoramidite
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CAS No:
104992-55-4
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Formula:
C53H66N7O8PSi
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Chemical Name:
Bz-rA Phosphoramidite
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Synonyms:
Bz-rA Phosphoramidite;DMT-2"O-TBDMS-Ra(Bz) Phosphoramidite;(2R,3R,4R,5R)-5-(6-Benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite;DMT-2"O-TBDMS-rA(bz) amidite;N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]purin-6-yl]benzamide;DMT-2"O-TBDMS-rA(bz) Pharmadite(R);DMT-2"O-TBDMS-rA(bz) Phosphoramidite, configured for ABI;DMT-2"O-TBDMS-rA(bz) Phosphoramidite, configured for MerMade;N-Benzoyl-5"-O-(4,4-Dimethoxytrityl)-2"-O-[(tert-butyl)dimethylsilyl]adenosine-3"-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite;C53H66N7O8PSi
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CAS No:
Bz-rA Phosphoramidite Use and Manufacturing
To a solution of 72 (12.0 g, 15.2 mmoi) in DIPEA (15 ml) and DCM (30 niL’) is added DMAP (744 mg, 6.09 rnrnol) and 2cyanoethyl JV.Ndiisopropylchlorophosphoramidite (5.41 g, 22.9 rnmoi) at 25 °C. After stirring for 2 hours, the mixture is purified directly by basic silica gel column chromatography (EAIPE 1/4 toi/1) to give A2 as a white solid (13.0 g. 86percent yield)Examples 12-18; These Examples illustrate the phosphitylation of several protected nucleoside reagents with 2-Cyanoethyl-N, N, N', N'-tetraisopropylphosphordiamidite in the presence of a Huenig's Base-TFA activator according to the present invention. Seven nucleoside reagents of the Formula III (below) were reacted with 2-Cyanoethyl-N, N, N', N'-tetraisopropylphosphordiamidite in the presence of a Huenig's Base-TFA activator according to the General Procedure for Examples 1-11, and the product yield calculated via one of two methods: (1) 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 percentyield of product in the mixture; or (2) the resulting product is purified on a short silica gel column using a methylacetate/toluene mixture (the concentration depending on the particular product being purified). The appropriate product fractions are concentrated under reduced pressure and solvent until an approximately 50percent solution of the desired amidite is obtained. This solution is added to about 5 to 25 equivalents of petroleum ether to precipitate the product which is filtered and washed with petroleum ether. The product is then dried, weighed, and the percent yield calculated.
Computed Properties
Molecular Weight:988.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:13
Rotatable Bond Count:22
Exact Mass:987.44797562
Monoisotopic Mass:987.44797562
Topological Polar Surface Area:164
Heavy Atom Count:70
Complexity:1630
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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