1-(5-O-tert-butyldiphenylsilyl-2-deoxy-4-C-methyl-β-D-threo-pentofuranosyl)thymine

Base Information

• Chemical Name: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-4-C-methyl-β-D-threo-pentofuranosyl)thymine
• CAS No.: 151989-77-4
• Molecular Formula: C₂₇H₃₄N₂O₅Si
• Molecular Weight: 494.663
• Mol file: 151989-77-4.mol

Synonyms:1-(5-O-tert-butyldiphenylsilyl-2-deoxy-4-C-methyl-β-D-threo-pentofuranosyl)thymine

Chemical Property of 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-4-C-methyl-β-D-threo-pentofuranosyl)thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-4-C-methyl-β-D-threo-pentofuranosyl)thymine

There total 5 articles about 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-4-C-methyl-β-D-threo-pentofuranosyl)thymine 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: 88.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 1-((2R,4R,5R)-4-hydroxy-5-hydroxymethyl-5-methyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (152141-66-7) → 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-4-C-methyl-β-D-threo-pentofuranosyl)thymine (151989-77-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1135/cccc19931668

Reference yield:

1-(2-deoxy-4-C-hydroxymethyl-α-L-erythro-pentofuranosyl)thymine (151767-33-8) → 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-4-C-methyl-β-D-threo-pentofuranosyl)thymine (151989-77-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / H₂SO₄ / acetone / 0.33 h / Ambient temperature

2: 84 percent / hexamethylphosphoric triamide, thionyl chloride / Ambient temperature

3: 81 percent / tributylstannane, 2,2'-azobis(2-methylpropionitrile) / toluene / 0.67 h / 100 °C

4: 86 percent / dowex 50 (H⁺ form) / methanol; H₂O / 2 h / Heating

5: 88 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; thionyl chloride; 2,2'-azobis(isobutyronitrile); Dowex 50 (H⁺ form); sulfuric acid; tri-n-butyl-tin hydride; In methanol; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1135/cccc19931668

Reference yield:

5-methyl-1-[(4aS,6R,7aR)-2,2,4a-trimethyltetrahydrofuro[3,2-d][1,3]dioxin-6-yl]-1H-pyrimidine-2,4-dione (151989-76-3) → 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-4-C-methyl-β-D-threo-pentofuranosyl)thymine (151989-77-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / dowex 50 (H⁺ form) / methanol; H₂O / 2 h / Heating

2: 88 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; Dowex 50 (H⁺ form); In methanol; water; N,N-dimethyl-formamide;

DOI:10.1135/cccc19931668

upstream raw materials:

tert-butylchlorodiphenylsilane

1-((2R,4R,5R)-4-hydroxy-5-hydroxymethyl-5-methyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

1-(2-deoxy-4-C-hydroxymethyl-α-L-erythro-pentofuranosyl)thymine

5-methyl-1-[(4aS,6R,7aR)-2,2,4a-trimethyltetrahydrofuro[3,2-d][1,3]dioxin-6-yl]-1H-pyrimidine-2,4-dione

Downstream raw materials:

1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine

1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-methanesulfonyl-4-C-methyl-β-D-threo-pentofuranosyl)thymine