(4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester
• CAS No.: 381233-12-1
• Molecular Formula: C₃₅H₃₅N₃O₁₀
• Molecular Weight: 657.677

Synonyms:(4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Chemical Property of (4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester

There total 2 articles about (4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid methyl 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: 66.0%

(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid monomethyl ester (263550-15-8) + 5'-amino-2',3'-di-O-benzyl-5'-deoxy-uridine (262286-59-9) → (4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester (381233-12-1)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1016/S0008-6215(01)00191-4

Reference yield:

dimethyl 2,3-O-benzylidene-L-tartrate (38270-72-3) → (4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester (381233-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / KOH / methanol; tetrahydrofuran / 15 h / 20 °C

2: 66 percent / HOBt; DCC / tetrahydrofuran; CH₂Cl₂ / 16 h / 0 - 20 °C

With potassium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0008-6215(01)00191-4

Reference yield: 91.0%

(4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester (381233-12-1) → (4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid (381233-13-2)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃; for 15h;

DOI:10.1016/S0008-6215(01)00191-4

upstream raw materials:

(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid monomethyl ester

5'-amino-2',3'-di-O-benzyl-5'-deoxy-uridine

dimethyl 2,3-O-benzylidene-L-tartrate

Downstream raw materials:

(4R,5R)-5-[(3',4'-di-O-benzyl-5'-deoxy-uridin-5'-yl)-carbamoyl]-2-phenyl-[1,3]dioxolane-4-carboxylic acid

(4R,5R)-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-{[2-(2'-N-acetylamino-4',5',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) ethyl]-amide}-5-[(3',4'-di-O-benzyl-5'-deoxyuridin-5'-yl)-amide]

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