150491-85-3

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 5116-24-5 2'-deoxy-5-(hydroxymethyl)uridine 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 951-78-0 2'-deoxyuridine 
• 1292210-10-6 3',5'-O-di-tert-butylsilyl-5-hydroxymethyl-2'-deoxyuridine 
• 1292210-09-3 3',5'-O-di-tert-butylsilyl-5-formyl-2'-deoxyuridine 
• 1292210-08-2 3',5'-O-di-tert-butylsilyl-5-iodo-2'-deoxyuridine 
• 1292210-07-1 3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-2'-deoxyuridine 
• 150491-84-2 5-tert-butyldimethylsiloxymethyl-2'-deoxyuridine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 

Downstream Products

• 1292210-15-1 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-2'-deoxyuridine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 

Relevant academic research and scientific papers

Syntheses of two 5-hydroxymethyl-2′-deoxycytidine phosphoramidites with TBDMS as the 5-hydroxymethyl protecting group and their incorporation into DNA

5-Hydroxymethylcytosine (5-hmC) is a newly discovered DNA base modification in mammalian genomic DNA that is proposed to be a major epigenetic mark. We report here the syntheses of two new versions of phosphoramidites III and IV from 5-iodo-2′-deoxyuridine in 18% and 32% overall yields, respectively, with TBDMS as the 5-hydroxyl protecting group. Phosphoramidites III and IV allow efficient incorporation of 5-hmC into DNA and a "one-step" deprotection procedure to cleanly remove all the protecting groups. A "two-step" deprotection strategy is compatible with ultramild DNA synthesis, which enables the synthesis of 5hmC-containing DNA with additional modifications.