1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine

Base Information

• Chemical Name: 1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine
• CAS No.: 906482-21-1
• Molecular Formula: C₂₃H₃₃N₃O₈Si
• Molecular Weight: 507.616
• Mol file: 906482-21-1.mol

Synonyms:1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine

Chemical Property of 1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine

There total 1 articles about 1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]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: 32.0%

2-Nitrobenzyl alcohol (612-25-9) + 1-[3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl]thymine (135911-57-8,128093-86-7) → 1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine (906482-21-1) + 1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-α-L-lyxofuranosyl]thymine

Guidance literature:

2-Nitrobenzyl alcohol; 1-[3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl]thymine; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h;

With zinc chloride diethyl ether; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1021/ol060987v

Reference yield: 89.0%

1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine (906482-21-1) → 1-[2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine (906482-23-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ol060987v

Reference yield:

1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine (906482-21-1) → Phosphorous acid (2R,3S,5R)-2-[(2-cyano-ethoxy)-methoxy-phosphanyloxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-nitro-benzyloxy)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

2: 1H-tetrazole; molecular sieves 4 Angstroem / acetonitrile / 1.5 h / 0 - 20 °C

With 1H-tetrazole; 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ol060987v

upstream raw materials:

2-Nitrobenzyl alcohol

1-[3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl]thymine

Downstream raw materials:

1-[2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine

1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine

1-[2-deoxy-3,5-di-O-(2-cyanoethylmethylphosphoryl)-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine