1-{2-O-[(2-bromoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N⁴-benzoylcytosine

Base Information

• Chemical Name: 1-{2-O-[(2-bromoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N⁴-benzoylcytosine
• CAS No.: 1042664-89-0
• Molecular Formula: C₃₁H₄₈BrN₃O₈Si₂
• Molecular Weight: 726.812

Synonyms:1-{2-O-[(2-bromoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N⁴-benzoylcytosine

Chemical Property of 1-{2-O-[(2-bromoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N⁴-benzoylcytosine

Chemical Property:

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Technology Process of 1-{2-O-[(2-bromoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N⁴-benzoylcytosine

There total 1 articles about 1-{2-O-[(2-bromoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N⁴-benzoylcytosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

2-(bromoethoxy)methyl acetate (89364-58-9) + 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine (69304-43-4) → 1-{2-O-[(2-bromoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N4-benzoylcytosine (1042664-89-0)

Guidance literature:

With tin(IV) chloride; In 1,2-dichloro-ethane; at -12 ℃; for 0.333333h;

DOI:10.1016/j.tet.2008.04.110

Reference yield: 94.0%

1-{2-O-[(2-bromoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N4-benzoylcytosine (1042664-89-0) → 1-{2-O-[(2-azidoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N4-benzoylcytosine (1042664-83-4)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

DOI:10.1016/j.tet.2008.04.110

Reference yield: 57.0%

1-{2-O-[(2-bromoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N4-benzoylcytosine (1042664-89-0) → 2'-O-(2-bromoethoxymethyl)-N(4)-benzoylcytidine (1309370-93-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.333333h;

DOI:10.1021/bc200097g

upstream raw materials:

2-(bromoethoxy)methyl acetate

1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N⁴-benzoylcytosine

Downstream raw materials:

1-{2-O-[(2-azidoethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N⁴-benzoylcytosine

2'-O-(2-bromoethoxymethyl)-5'-O-(4,4'-dimethoxytrityl)-β-N(4)-benzoylcytidine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)

2'-O-(2-bromoethoxymethyl)-N⁽⁴⁾-benzoylcytidine

2'-O-(2-bromoethoxymethyl)-5'-O-(4,4'-dimethoxytrityl)-N⁽⁴⁾-benzoylcytidine

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