5'-TBDMS-2,3'-ANHYDRO-2'-DEOXYURIDINE

Base Information

• Chemical Name: 5'-TBDMS-2,3'-ANHYDRO-2'-DEOXYURIDINE
• CAS No.: 124288-67-1
• Molecular Formula: C₁₅H₂₄N₂O₄Si
• Molecular Weight: 324.452
• Mol file: 124288-67-1.mol

Synonyms:2,5-Methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one,3-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2,3-dihydro-, [2R-(2a,3b,5a)]-

Chemical Property of 5'-TBDMS-2,3'-ANHYDRO-2'-DEOXYURIDINE

Chemical Property:

• PSA: 62.58000
• LogP: 2.31360

Purity/Quality:

98%min ^*data from raw suppliers

5'-TBDMS-2,3'-ANHYDRO-2'-DEOXYURIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5'-TBDMS-2,3'-ANHYDRO-2'-DEOXYURIDINE

There total 5 articles about 5'-TBDMS-2,3'-ANHYDRO-2'-DEOXYURIDINE 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: 94.0%

1-((2R,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (76223-04-6) → 2,3'-anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-1-(β-D-threo-pentofuranosyl)uracil (124288-67-1)

Guidance literature:

With sodium hydride; N,N`-sulfuryldiimidazole; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1080/00397910008086944

Reference yield:

2'-deoxyuridine (951-78-0,63844-76-8) → 2,3'-anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-1-(β-D-threo-pentofuranosyl)uracil (124288-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / -10 °C

2: 68 percent / triphenylphosphine; diisopropyl azodicarboxylate / 20 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide;

DOI:10.1002/hc.20288

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2,3'-anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-1-(β-D-threo-pentofuranosyl)uracil (124288-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / -10 °C

2: 68 percent / triphenylphosphine; diisopropyl azodicarboxylate / 20 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide;

DOI:10.1002/hc.20288

upstream raw materials:

1-((2R,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

tert-butyldimethylsilyl chloride

(2R)-3t-hydroxymethyl-2,3-dihydro-2r,5c-methano-pyrimido[2,1-b][1,5,3]dioxazepin-9-one

2'-deoxyuridine

Downstream raw materials:

3'-isocyano-2',3'-dideoxyuridine

Refernces

• 1、 No,Dong Seong Shin,Bok Ju Song,Ahn,Ha. "A facile one-pot synthesis of 2,3'-anhydro-2'-deoxyuridines via 3'-O-imidazolylsulfonates". . p. 3873 - 3882. Retrieved 2007/10/03.
• 2、 Hiebl, Johann,Zbiral, Erich,Balzarini, Jan,Clercq, Erik De. "Synthesis, Antiretrovirus Effects, and Phosphorylation Kinetics of 3'-Isocyano-3'-deoxythymidine and 3'-Isocyano-2',3'-dideoxyuridine". . p. 845 - 848. Retrieved 2007/10/02.