1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(hydroxy-phenyl-methyl)-5-methyl-dihydro-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(hydroxy-phenyl-methyl)-5-methyl-dihydro-pyrimidine-2,4-dione
• CAS No.: 187979-95-9
• Molecular Formula: C₂₉H₅₀N₂O₆Si₂
• Molecular Weight: 578.897
• Mol file: 187979-95-9.mol

Synonyms:1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(hydroxy-phenyl-methyl)-5-methyl-dihydro-pyrimidine-2,4-dione

Chemical Property of 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(hydroxy-phenyl-methyl)-5-methyl-dihydro-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(hydroxy-phenyl-methyl)-5-methyl-dihydro-pyrimidine-2,4-dione

There total 3 articles about 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(hydroxy-phenyl-methyl)-5-methyl-dihydro-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: 70.0%

benzaldehyde (100-52-7) + 3′,5′-bis-O-[(tert-butyl)dimethylsilyl]-5,6-dihydrothymidine (187979-92-6) → 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(hydroxy-phenyl-methyl)-5-methyl-dihydro-pyrimidine-2,4-dione (187979-95-9)

Guidance literature:

With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 2h;

DOI:10.1021/ja9533510

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(hydroxy-phenyl-methyl)-5-methyl-dihydro-pyrimidine-2,4-dione (187979-95-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / hydrogen / rhodium on alumina / methanol; H₂O / 48 h / 2585.7 Torr

2: 88 percent / pyridine / 24 h / 40 °C

3: 70 percent / sec-BuLi / tetrahydrofuran; cyclohexane / 2 h / -78 °C

With pyridine; hydrogen; sec.-butyllithium; Rh/Al₂O₃; In tetrahydrofuran; methanol; cyclohexane; water;

DOI:10.1021/ja9533510

Reference yield:

5,6-dihydrothymidine (5627-00-9) → 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(hydroxy-phenyl-methyl)-5-methyl-dihydro-pyrimidine-2,4-dione (187979-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / pyridine / 24 h / 40 °C

2: 70 percent / sec-BuLi / tetrahydrofuran; cyclohexane / 2 h / -78 °C

With pyridine; sec.-butyllithium; In tetrahydrofuran; cyclohexane;

DOI:10.1021/ja9533510

upstream raw materials:

benzaldehyde

3′,5′-bis-O-[(tert-butyl)dimethylsilyl]-5,6-dihydrothymidine

5,6-dihydrothymidine

thymidine

Downstream raw materials:

5-Benzoyl-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-dihydro-pyrimidine-2,4-dione

5-Benzoyl-1-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-dihydro-pyrimidine-2,4-dione