1-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,4-b]furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,4-b]furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 629613-68-9
• Molecular Formula: C₂₈H₃₄N₂O₅Si
• Molecular Weight: 506.674
• Mol file: 629613-68-9.mol

Synonyms:1-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,4-b]furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property of 1-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,4-b]furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,4-b]furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

There total 21 articles about 1-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,4-b]furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 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:

thiocarbonic acid O-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b]furan-3-yl] ester O-phenyl ester → 1-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,4-b]furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (629613-68-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 100 ℃; for 3h;

DOI:10.1016/S0960-894X(03)00730-3

Reference yield:

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol (69832-48-0) → 1-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,4-b]furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (629613-68-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 80 percent / NaH; TBAI / tetrahydrofuran / 16 h / 20 °C

2: aq. AcOH / 2 h / 55 °C

3: aq. NaIO₄ / ethanol / 0.5 h / 0 °C

4: aq. NaOH / dioxane / 72 h / 20 °C

5: 73 percent / pyridine / 14 h / 20 °C

6: 85 percent / H₂ / Pd(OH)2 / ethanol / 14 h / 20 °C

7: NaH / tetrahydrofuran / 1 h / 55 °C

8: aq. NaOH / 12 h / Heating

9: 91 percent / pyridine / 12 h

10: aq. HCO₂H / 2 h / 55 °C

11: pyridine / 16 h / 20 °C

12: TMSOTf / acetonitrile / 4 h / 60 °C

13: 93 percent / NH₄OH / methanol / 14 h / 20 °C

14: 84 percent / imidazole / dimethylformamide / 16 h / 20 °C

15: DMAP; Et₃N / acetonitrile / 2 h / 0 °C

16: Bu₃SnH; AIBN / toluene / 3 h / 100 °C

With pyridine; 1H-imidazole; dmap; ammonium hydroxide; sodium hydroxide; sodium periodate; formic acid; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; hydrogen; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; N,N-dimethyl-formamide; toluene; acetonitrile; 4: Cannizarrro reaction;

DOI:10.1016/S0960-894X(03)00730-3

Reference yield:

O1,O2;O5,O6-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose (21665-16-7) → 1-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,4-b]furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (629613-68-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 3 h / 20 °C

1.2: 77 percent / H₂O₂; aq. NaOH / 2 h / 20 °C

2.1: 80 percent / NaH; TBAI / tetrahydrofuran / 16 h / 20 °C

3.1: aq. AcOH / 2 h / 55 °C

4.1: aq. NaIO₄ / ethanol / 0.5 h / 0 °C

5.1: aq. NaOH / dioxane / 72 h / 20 °C

6.1: 73 percent / pyridine / 14 h / 20 °C

7.1: 85 percent / H₂ / Pd(OH)2 / ethanol / 14 h / 20 °C

8.1: NaH / tetrahydrofuran / 1 h / 55 °C

9.1: aq. NaOH / 12 h / Heating

10.1: 91 percent / pyridine / 12 h

11.1: aq. HCO₂H / 2 h / 55 °C

12.1: pyridine / 16 h / 20 °C

13.1: TMSOTf / acetonitrile / 4 h / 60 °C

14.1: 93 percent / NH₄OH / methanol / 14 h / 20 °C

15.1: 84 percent / imidazole / dimethylformamide / 16 h / 20 °C

16.1: DMAP; Et₃N / acetonitrile / 2 h / 0 °C

17.1: Bu₃SnH; AIBN / toluene / 3 h / 100 °C

With pyridine; 1H-imidazole; dmap; ammonium hydroxide; sodium hydroxide; sodium periodate; formic acid; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; hydrogen; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Cannizarrro reaction;

DOI:10.1016/S0960-894X(03)00730-3

upstream raw materials:

tert-butylchlorodiphenylsilane

1-((2R,3R,3aS,6aS)-3-Hydroxy-6a-hydroxymethyl-hexahydro-furo[3,4-b]furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Acetic acid (2R,3R,3aS,6aR)-3-acetoxy-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furo[3,4-b]furan-6a-ylmethyl ester

1-[6a-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-hexahydro-furo[3,4-b]furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Refernces

• 1、 Chun, Moon Woo,Kim, Myong Jung,Kim, Hea Ok,Moon, Hyung Ryong,Kim, Hee-Doo,Kim, Joong Hyup,Jeong, Lak Shin. "Synthesis and biological evaluation of pyrimidine nucleosides fused with 3′,4′-tetrahydrofuran ring". . p. 719 - 721. Retrieved 2007/10/03.