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

Base Information

• Chemical Name: [(2S,3R,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid
• CAS No.: 171762-80-4
• Molecular Formula: C₂₉H₃₆N₂O₇Si
• Molecular Weight: 552.7
• Mol file: 171762-80-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about [(2S,3R,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid 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: 92.0%

[(2S,3R,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetaldehyde (171762-79-1) → [(2S,3R,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid (171762-80-4)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; for 30h; Ambient temperature;

Reference yield:

O-2,2'-cyclo-5-methyluridine (22423-26-3) → [(2S,3R,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid (171762-80-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 72 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

2: 82 percent / Et₃N, DMAP, pyridine / CH₂Cl₂ / 40 h / Ambient temperature

3: 79 percent / AIBN / benzene / 20 h / Heating

4: 90 percent / aq. NaOH / tetrahydrofuran / 5 h / Ambient temperature

5: 92 percent / DBU / acetonitrile / 18 h / Ambient temperature

6: 83 percent / PPh₃, diisopropylazodicarboxylate / toluene / 50 h / Ambient temperature

7: 92 percent / NaOMe / methanol / 1 h / Ambient temperature

8: 94 percent / NaH / tetrahydrofuran / 17 h / Ambient temperature

9: 61 percent / OsO₄, N-methylmorpholine-N-oxide, H₂O / acetone / 18 h / Ambient temperature

10: 83 percent / H₂ / 10percent Pd/C / methanol / 18 h / 760 Torr / Ambient temperature

11: 81 percent / aq. NaIO₄ / dioxane / 18 h / Ambient temperature

12: 92 percent / aq. NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol / 30 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; water; hydrogen; sodium methylate; sodium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → [(2S,3R,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid (171762-80-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 72 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

2: 82 percent / Et₃N, DMAP, pyridine / CH₂Cl₂ / 40 h / Ambient temperature

3: 79 percent / AIBN / benzene / 20 h / Heating

4: 90 percent / aq. NaOH / tetrahydrofuran / 5 h / Ambient temperature

5: 92 percent / DBU / acetonitrile / 18 h / Ambient temperature

6: 83 percent / PPh₃, diisopropylazodicarboxylate / toluene / 50 h / Ambient temperature

7: 92 percent / NaOMe / methanol / 1 h / Ambient temperature

8: 94 percent / NaH / tetrahydrofuran / 17 h / Ambient temperature

9: 61 percent / OsO₄, N-methylmorpholine-N-oxide, H₂O / acetone / 18 h / Ambient temperature

10: 83 percent / H₂ / 10percent Pd/C / methanol / 18 h / 760 Torr / Ambient temperature

11: 81 percent / aq. NaIO₄ / dioxane / 18 h / Ambient temperature

12: 92 percent / aq. NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol / 30 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; water; hydrogen; sodium methylate; sodium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;

upstream raw materials:

[(2S,3R,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetaldehyde

O-2,2'-cyclo-5-methyluridine

tert-butylchlorodiphenylsilane

5'-O-tert-butyldiphenylsilyl-O²-2'-anhydro-5-methyluridine

Downstream raw materials:

C₅₅H₆₇N₅O₁₀Si₂

C₄₄H₄₉N₅O₁₂