1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-azido-2-deoxy-β-D-arabinofuranosyl]-N³-benzoyluracil

Base Information

• Chemical Name: 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-azido-2-deoxy-β-D-arabinofuranosyl]-N³-benzoyluracil
• CAS No.: 125126-00-3
• Molecular Formula: C₂₈H₄₁N₅O₇Si₂
• Molecular Weight: 615.834

Synonyms:1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-azido-2-deoxy-β-D-arabinofuranosyl]-N³-benzoyluracil

Chemical Property of 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-azido-2-deoxy-β-D-arabinofuranosyl]-N³-benzoyluracil

Chemical Property:

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Technology Process of 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-azido-2-deoxy-β-D-arabinofuranosyl]-N³-benzoyluracil

There total 7 articles about 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-azido-2-deoxy-β-D-arabinofuranosyl]-N³-benzoyluracil 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: 74.0%

3-benzoyl-1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]pyrimidine-2,4(1H,3H)-dione (86988-35-4) → 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-azido-2-deoxy-β-D-arabinofuranosyl]-N3-benzoyluracil (125126-00-3)

Guidance literature:

With diphenylphosphoranyl azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1021/jm00107a018

Reference yield:

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (69304-38-7) → 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-azido-2-deoxy-β-D-arabinofuranosyl]-N3-benzoyluracil (125126-00-3)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

2: CH₂Cl₂ / 2 h / 20 °C

3: 3.5 g / p-toluenesulfonic acid / CH₂Cl₂; dioxane / 0.03 h / 20 °C

4: 70 percent / triphenylphosphine; diethyl azodicarboxylate; diphenyl azidophosphate

With diphenyl phosphoryl azide; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; dichloromethane; 1: silylation / 2: Acylation / 3: desilylation / 4: Mitsunobu reaction;

Reference yield:

benzoyl chloride (98-88-4) → 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-azido-2-deoxy-β-D-arabinofuranosyl]-N3-benzoyluracil (125126-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / triethylamine / CH₂Cl₂

2: 62 percent / diphenylphosphorazide, triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature

With diphenyl phosphoryl azide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.37.1659

upstream raw materials:

3-benzoyl-1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]pyrimidine-2,4(1H,3H)-dione

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

uridine

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Downstream raw materials:

cytarazid

N-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-yl]-2,2,2-trifluoro-acetamide

1-[5-O-(4,4'-dimethoxytrityl)-2-amino-2-deoxy-β-D-arabinofuranosyl]uracil

1-[5-O-(4,4'-dimethoxytrityl)-2-azido-2-deoxy-β-D-arabinofuranosyl]uracil

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