phosphoric acid 4,5-dimethoxy-2-nitro-benzyl ester 3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: phosphoric acid 4,5-dimethoxy-2-nitro-benzyl ester 3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 295311-84-1
• Molecular Formula: C₂₉H₃₆N₅O₁₆P
• Molecular Weight: 741.602

Synonyms:

Chemical Property of phosphoric acid 4,5-dimethoxy-2-nitro-benzyl ester 3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of phosphoric acid 4,5-dimethoxy-2-nitro-benzyl ester 3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

There total 7 articles about phosphoric acid 4,5-dimethoxy-2-nitro-benzyl ester 3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-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:

5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) → phosphoric acid 4,5-dimethoxy-2-nitro-benzyl ester 3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (295311-84-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dicyclohexylcarbodiimide / diethyl ether / 3 h / 20 °C

1.2: N-methylimidazole / pyridine / 0.5 h

2.1: 0.22 g / acetic acid; H₂O / 2 h / 40 °C

3.1: 75 percent / triisopropylbenzenesulfonyl chloride; M-methylimidazole / pyridine

4.1: CsF / acetonitrile / 0.33 h / 50 °C

5.1: N₂H₄*H₂O

6.1: acetic acid; H₂O / 0.5 h

With 1-methyl-1H-imidazole; triisopropylbenzenesulfonyl chloride; hydrazine hydrate; dicyclohexyl-carbodiimide; cesium fluoride; In pyridine; diethyl ether; water; acetic acid; acetonitrile; 1.1: Addition / 1.2: Condensation / 2.1: acidolysis / 3.1: Esterification / 4.1: transesterification / 5.1: hyrazinolysis / 6.1: acidolysis;

DOI:10.1007/BF02786343

Reference yield:

3'-O-levulinoylthymidine (78635-98-0) → phosphoric acid 4,5-dimethoxy-2-nitro-benzyl ester 3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (295311-84-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / triisopropylbenzenesulfonyl chloride; M-methylimidazole / pyridine

2: CsF / acetonitrile / 0.33 h / 50 °C

3: N₂H₄*H₂O

4: acetic acid; H₂O / 0.5 h

With 1-methyl-1H-imidazole; triisopropylbenzenesulfonyl chloride; hydrazine hydrate; cesium fluoride; In pyridine; water; acetic acid; acetonitrile; 1: Esterification / 2: transesterification / 3: hyrazinolysis / 4: acidolysis;

DOI:10.1007/BF02786343

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-3'-O-levulinoyl-2'-deoxythymidine (93134-37-3) → phosphoric acid 4,5-dimethoxy-2-nitro-benzyl ester 3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (295311-84-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 0.22 g / acetic acid; H₂O / 2 h / 40 °C

2: 75 percent / triisopropylbenzenesulfonyl chloride; M-methylimidazole / pyridine

3: CsF / acetonitrile / 0.33 h / 50 °C

4: N₂H₄*H₂O

5: acetic acid; H₂O / 0.5 h

With 1-methyl-1H-imidazole; triisopropylbenzenesulfonyl chloride; hydrazine hydrate; cesium fluoride; In pyridine; water; acetic acid; acetonitrile; 1: acidolysis / 2: Esterification / 3: transesterification / 4: hyrazinolysis / 5: acidolysis;

DOI:10.1007/BF02786343

upstream raw materials:

3'-O-levulinoylthymidine

5'-O-(4,4'-dimethoxytrityl)-3'-O-levulinoyl-2'-deoxythymidine

4-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphate

5'-O-(4-4'-dimethoxytrityl)thymidine

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