Benzoic acid (2R,3S,5R)-2-[[(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenoxy)-phosphoryloxymethyl]-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,5R)-2-[[(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenoxy)-phosphoryloxymethyl]-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 72952-22-8
• Molecular Formula: C₄₆H₄₀ClN₈O₁₂P
• Molecular Weight: 963.297

Synonyms:

Chemical Property of Benzoic acid (2R,3S,5R)-2-[[(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenoxy)-phosphoryloxymethyl]-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

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Technology Process of Benzoic acid (2R,3S,5R)-2-[[(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenoxy)-phosphoryloxymethyl]-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

There total 10 articles about Benzoic acid (2R,3S,5R)-2-[[(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenoxy)-phosphoryloxymethyl]-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester 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:

4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine (67219-55-0) → Benzoic acid (2R,3S,5R)-2-[[(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenoxy)-phosphoryloxymethyl]-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester (72952-22-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) pyridine; 2.) 5percent aq. NH₄HCO₃ / 1.) dioxane, 30 min at room temp.; 2.) dioxane, cooling

2: 1-(mesitylsulfonyl)tetrazole / pyridine / 1 h / Ambient temperature

3: 2percent benzenesulfonic acid / CHCl₃; methanol / Ambient temperature

With pyridine; 1-mesitylsulfonyl-1H-tetrazole; ammonium bicarbonate; benzenesulfonic acid; In pyridine; methanol; chloroform;

Reference yield:

(p-chlorophenyl) (β-cyanoethyl) phosphorochloridate (69507-62-6) → Benzoic acid (2R,3S,5R)-2-[[(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenoxy)-phosphoryloxymethyl]-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester (72952-22-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1-methylimidazole / acetonitrile / 2 h / 20 °C

2: triethylamine

3: 1-(mesitylsulfonyl)tetrazole / pyridine / 1 h / Ambient temperature

4: 2percent benzenesulfonic acid / CHCl₃; methanol / Ambient temperature

With 1-methyl-1H-imidazole; 1-mesitylsulfonyl-1H-tetrazole; triethylamine; benzenesulfonic acid; In pyridine; methanol; chloroform; acetonitrile;

Reference yield:

C43H38ClN3O10P(1-) → Benzoic acid (2R,3S,5R)-2-[[(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenoxy)-phosphoryloxymethyl]-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester (72952-22-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-(mesitylsulfonyl)tetrazole / pyridine / 1 h / Ambient temperature

2: 2percent benzenesulfonic acid / CHCl₃; methanol / Ambient temperature

With 1-mesitylsulfonyl-1H-tetrazole; benzenesulfonic acid; In pyridine; methanol; chloroform;

upstream raw materials:

(p-chlorophenyl) (β-cyanoethyl) phosphorochloridate

N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-2'-deoxyadenosine 3'-benzoate

N⁴-benzoyl-5'-O-(p,p'-dimethoxytrityl)deoxycytidine 3'-<(p-chlorophenyl)(β-cyanoethyl)phosphate>

benzoyl chloride

Downstream raw materials:

C₈₇H₇₉Cl₂N₁₃O₂₁P₂

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