375345-66-7

Upstream product

• 2592-95-2 benzotriazol-1-ol 
• 701-99-5 Phenoxyacetyl chloride 

Downstream Products

• 110522-71-9 N²-phenoxyacetyl-2’-deoxyguanosine 
• 121076-16-2 5'-O-dimethoxytrityl-N₆-phenoxyacetyladenosine 
• 200264-32-0 Carbonic acid 1-(3,5-dimethoxy-phenyl)-2-oxo-2-phenyl-ethyl ester (2R,3S,5R)-3-hydroxy-5-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 
• 226558-71-0 N-[9-(2-dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-2-phenoxy-acetamide 
• 121058-84-2 5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N2-phenoxyacetylguanosine 
• 121058-83-1 5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N⁶-phenoxyacetyladenosine 
• 121058-81-9 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-N₂-phenoxyacetylguanosine 
• 119824-66-7 N²-(phenoxyacetyl)guanosine 

Relevant academic research and scientific papers

Proofing of Photolithographic DNA Synthesis with 3′,5′-Dimethoxybenzoinyloxycarbonyl-Protected Deoxynucleoside Phosphoramidites

We have evaluated in a microchip format the photochemical solid-phase phosphoramidite DNA synthesis method we previously developed. A set of nucleoside building blocks with "easy-off" base protecting groups was prepared bearing photolabile 5′-O-dimethoxybenzoincarbonate (DMBOC) groups. Photolysis rates and cycle yields for these DMBOC-protected nucleotides covalently attached to planar, derivatized glass surfaces were determined by fluorescence imaging-based methods earlier developed by McGall et al. and described in detail elsewhere. Data were obtained for both 280/310 and 365/400 nm irradiation in a range of solvents. Deprotection of the DMBOC occurs fastest in a nonpolar medium or without solvent. The coupling efficiency of these amidites in the synthesis of homopolymers was determined to be in the range 80-97%, with purines generally showing lower efficiency than pyrimidines. These DMBOC-protected monomers were used to prepare a 4 × 4 array of 16 decanucleotides of the sequence 5′-AAXTAXCTAC-chip, where X = A, C, G, or T. The array was hybridized with a target deoxyeicosanucleotide of the sequence fluorescein-5′-CTGAACGGTAGCATCTTGAC. Surface fluorescence imaging demonstrated sequence-specific hybridization to this probe.

High yield protection of purine ribonucleosides for phosphoramidite RNA synthesis

We report high yield procedures for protection of purine ribonucleosides based on a reaction which allows concomitant highly regiospecific 2'-silylation and 3'-phosphitylation. Subsequent cleavage of the H-phosphonate monoester moiety without silyl migration provides intermediates ready for phosphitylation by standard methods to give fully protected phosphoramidites.