3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

Base Information

• Chemical Name: 3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propionic acid methyl ester
• CAS No.: 146557-86-0
• Molecular Formula: C₂₉H₃₆N₂O₆Si
• Molecular Weight: 536.7

Synonyms:3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

Chemical Property of 3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

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Technology Process of 3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

There total 3 articles about 3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propionic 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: 94.0%

(E)-3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acrylic acid methyl ester → 3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propionic acid methyl ester (146557-86-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 1.5h; Ambient temperature;

DOI:10.1016/S0960-894X(97)00269-2

Reference yield:

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (83467-48-5) → 3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propionic acid methyl ester (146557-86-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / DCC, pyridinium trifluoroacetate, DMSO / 2 h / Ambient temperature

2: 90 percent / CH₂Cl₂ / 1.5 h / 0 °C

3: 94 percent / H₂ / 10percent Pd/C / methanol / 1.5 h / Ambient temperature

With hydrogen; pyridinium trifluroacetate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/S0960-894X(97)00269-2

Reference yield:

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil (146604-43-5) → 3-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propionic acid methyl ester (146557-86-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / CH₂Cl₂ / 1.5 h / 0 °C

2: 94 percent / H₂ / 10percent Pd/C / methanol / 1.5 h / Ambient temperature

With hydrogen; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/S0960-894X(97)00269-2

upstream raw materials:

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil

Downstream raw materials:

3-[(2R,3S,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-propionic acid methyl ester

3-[(2R,3S,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-propionic acid

3-Benzyloxymethyl-1-{(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-[3-oxo-4-(triphenyl-λ⁵-phosphanylidene)-butyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

C₆₃H₈₁N₇O₁₀Si₂

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