N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

Base Information

• Chemical Name: N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine
• CAS No.: 1293390-53-0
• Molecular Formula: C₃₅H₅₅N₃O₁₀Si₂
• Molecular Weight: 734.007

Synonyms:N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

Chemical Property of N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

Chemical Property:

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Technology Process of N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

There total 6 articles about N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine 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: 60.0%

4-methoxy-2,6-dihydropyran (17327-22-9) + N4-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (1293390-47-2) → N4-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (1293390-53-0)

Guidance literature:

With (1S)-10-camphorsulfonic acid; In dichloromethane; at 20 ℃; for 18h; Molecular sieve;

DOI:10.1002/hlca.201000403

Reference yield:

3-methyl-1-(phenoxyacetyl)-1H-imidazol-3-ium chloride → N4-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (1293390-53-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,1,1,3,3,3-hexamethyl-disilazane / 4 h / Reflux

1.2: 20.5 h / 4 - 20 °C

1.3: 4 h / 20 °C

2.1: pyridine / 18 h / 20 °C

3.1: (1S)-10-camphorsulfonic acid / dichloromethane / 18 h / 20 °C / Molecular sieve

With pyridine; (1S)-10-camphorsulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

DOI:10.1002/hlca.201000403

Reference yield:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) → N4-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (1293390-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 18 h / 20 °C

2: (1S)-10-camphorsulfonic acid / dichloromethane / 18 h / 20 °C / Molecular sieve

With pyridine; (1S)-10-camphorsulfonic acid; In dichloromethane;

DOI:10.1002/hlca.201000403

upstream raw materials:

4-methoxy-2,6-dihydropyran

N⁴-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

Phenoxyacetyl chloride

Downstream raw materials:

N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine

N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 5'-[2-(2-nitrophenyl)propyl carbonate]

N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 3'-(2-cyanoethyl N,N-diisopropylphoshoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]

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