Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[(2R,3S,5R)-3-(2-methoxy-acetoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[(2R,3S,5R)-3-(2-methoxy-acetoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 150931-30-9
• Molecular Formula: C₃₇H₃₉N₅O₁₃
• Molecular Weight: 761.742

Synonyms:Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[(2R,3S,5R)-3-(2-methoxy-acetoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[(2R,3S,5R)-3-(2-methoxy-acetoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[(2R,3S,5R)-3-(2-methoxy-acetoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester

There total 3 articles about Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[(2R,3S,5R)-3-(2-methoxy-acetoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethoxy]-tetrahydro-furan-2-ylmethyl 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: 90.0%

(5'-O,4-N)-dibenzoyl-3'-O-acetyloxymethyl-2'-deoxycytidine (142730-08-3) + O3'-methoxyacetyl-thymidine (57064-86-5) → Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[(2R,3S,5R)-3-(2-methoxy-acetoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester (150931-30-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)79605-5

Reference yield:

(5'-O,4-N)-dibenzoyl-2'-deoxycytidine (4803-92-3) → Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[(2R,3S,5R)-3-(2-methoxy-acetoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester (150931-30-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / P₂O₅ / BF₃*Et₂O / dioxane / 2 h / 20 °C

2: 90 percent / CF₃SO₂H / acetic acid / 1.5 h / 0 °C

3: 90 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 1.5 h / 20 °C

With trifluoromethanesulfinic acid; trimethylsilyl trifluoromethanesulfonate; phosphorus pentoxide; boron trifluoride diethyl etherate; In 1,4-dioxane; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)79605-5

Reference yield:

Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-methoxymethoxy-tetrahydro-furan-2-ylmethyl ester (104768-98-1) → Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[(2R,3S,5R)-3-(2-methoxy-acetoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethoxy]-tetrahydro-furan-2-ylmethyl ester (150931-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / CF₃SO₂H / acetic acid / 1.5 h / 0 °C

2: 90 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 1.5 h / 20 °C

With trifluoromethanesulfinic acid; trimethylsilyl trifluoromethanesulfonate; In acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)79605-5

upstream raw materials:

(5'-O,4-N)-dibenzoyl-3'-O-acetyloxymethyl-2'-deoxycytidine

O^3'-methoxyacetyl-thymidine

Benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-methoxymethoxy-tetrahydro-furan-2-ylmethyl ester

(5'-O,4-N)-dibenzoyl-2'-deoxycytidine

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