Phenyl-phosphonic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 2-((2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl ester

Base Information

• Chemical Name: Phenyl-phosphonic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 2-((2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl ester
• CAS No.: 119827-59-7
• Molecular Formula: C₂₃H₃₁N₂O₁₃P
• Molecular Weight: 574.478

Synonyms:

Chemical Property of Phenyl-phosphonic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 2-((2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl ester

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Technology Process of Phenyl-phosphonic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 2-((2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl ester

There total 11 articles about Phenyl-phosphonic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 2-((2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl 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: 80.0%

Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(2-{[(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phenyl-phosphinoyloxy}-ethyl)-tetrahydro-pyran-3-yl ester → Phenyl-phosphonic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 2-((2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl ester (119827-59-7,119905-93-0)

Guidance literature:

With ammonia; for 16h; Ambient temperature;

Reference yield:

(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-propene (82659-53-8) → Phenyl-phosphonic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 2-((2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl ester (119827-59-7,119905-93-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / OsO₄, Na periodate / H₂O; dioxane / 1 h / 20 °C

2: 49 percent / Na borohydride / tetrahydrofuran; propan-2-ol / 0.5 h / 0 °C

3: 73 percent / N-methylimidazole / pyridine

4: methanolic ammonia

With 1-methyl-1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; ammonia; In tetrahydrofuran; 1,4-dioxane; pyridine; water; isopropyl alcohol;

DOI:10.1016/S0040-4039(00)80636-X

Reference yield:

2-C-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal (119827-44-0) → Phenyl-phosphonic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 2-((2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl ester (119827-59-7,119905-93-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 49 percent / Na borohydride / tetrahydrofuran; propan-2-ol / 0.5 h / 0 °C

2: 73 percent / N-methylimidazole / pyridine

3: methanolic ammonia

With 1-methyl-1H-imidazole; sodium tetrahydroborate; ammonia; In tetrahydrofuran; pyridine; isopropyl alcohol;

DOI:10.1016/S0040-4039(00)80636-X

upstream raw materials:

C₄₅H₄₇N₂O₁₉P

(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-propene

2-C-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal

3,7-anhydro-4,5,6,8-tetra-O-acetyl-2-deoxy-D-erythro-L-gulo-octitol

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