1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]thymine

Base Information

• Chemical Name: 1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]thymine
• CAS No.: 166955-29-9
• Molecular Formula: C₂₆H₃₂N₂O₅Si
• Molecular Weight: 480.636
• Mol file: 166955-29-9.mol

Synonyms:1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]thymine

Chemical Property of 1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-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-β-D-erythro-pentofuranosyl]thymine

There total 1 articles about 1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-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: 78.0%

5'-O-(tert-butyldiphenylsilyl)-3'-keto-2'-deoxythymidine (305819-88-9) → 5'-O-tert-butyldiphenylsilylthymidine (101527-40-6) + 1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]thymine (166955-29-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.166667h;

DOI:10.1002/jccs.200100139

Reference yield: 88.0%

N-hydroxyphthalimide (524-38-9) + 1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]thymine (166955-29-9) → 5'-O-tert-butyldiphenylsilyl-3'-O-phthalimido-thymidine (398456-05-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1002/jccs.200100139

Reference yield:

1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]thymine (166955-29-9) → 3'-O-amino-5'-O-tert-butyldiphenylsilyl-thymidine (398456-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran / 3 h / 0 °C

2: 87 percent / methyl hydrazine / CH₂Cl₂ / 2 h / -10 - 0 °C

With triphenylphosphine; methylhydrazine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1: Mitsunobu reaction;

DOI:10.1002/jccs.200100139

upstream raw materials:

5'-O-(tert-butyldiphenylsilyl)-3'-keto-2'-deoxythymidine

Downstream raw materials:

5'-O-tert-butyldiphenylsilyl-3'-O-phthalimido-thymidine

3'-O-amino-5'-O-tert-butyldiphenylsilyl-thymidine

C₅₂H₆₁N₅O₉Si₂

C₅₂H₆₃N₅O₉Si₂