N⁴-benzoyl-1-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine
• CAS No.: 869347-12-6
• Molecular Formula: C₂₈H₄₂BrN₃O₅SSi₂
• Molecular Weight: 668.8

Synonyms:N⁴-benzoyl-1-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

Chemical Property of N⁴-benzoyl-1-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

Chemical Property:

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Technology Process of N⁴-benzoyl-1-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

There total 2 articles about N⁴-benzoyl-1-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine 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:

C28H41N3O5SSi2 → N4-benzoyl-1-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (869347-12-6)

Guidance literature:

With boron trifluoride diethyl etherate; lithium bromide; In 1,4-dioxane; diethyl ether; at 50 ℃;

DOI:10.1021/jo051248f

Reference yield:

N4-benzoyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-36-6) → N4-benzoyl-1-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (869347-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoromethanesulfonic anhydride; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

2: 3.6 g / LiBr; BF₃*OEt₂ / dioxane; diethyl ether / 50 °C

With dmap; boron trifluoride diethyl etherate; trifluoromethanesulfonic acid anhydride; lithium bromide; In 1,4-dioxane; diethyl ether; dichloromethane;

DOI:10.1021/jo051248f

Reference yield: 95.0%

N4-benzoyl-1-[2-bromo-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (869347-12-6) → N-(2-oxo-1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyltetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1,2-dihydropyrimidin-4-yl)benzamide (869347-13-7)

Guidance literature:

With 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; tri-n-butyl-tin hydride; In dichloromethane; at 20 ℃;

DOI:10.1021/jo051248f

upstream raw materials:

N⁴-benzoyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

Downstream raw materials:

N-(2-oxo-1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyltetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1,2-dihydropyrimidin-4-yl)benzamide

N-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)pyrimidin-2(1H)-one

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