2',3'-bis(O-tert-butyldimethylsilyl)-3-(benzyloxymethyl)uridine-5'-aldehyde

Base Information

• Chemical Name: 2',3'-bis(O-tert-butyldimethylsilyl)-3-(benzyloxymethyl)uridine-5'-aldehyde
• CAS No.: 1346620-21-0
• Molecular Formula: C₂₉H₄₆N₂O₇Si₂
• Molecular Weight: 590.864
• Mol file: 1346620-21-0.mol

Synonyms:2',3'-bis(O-tert-butyldimethylsilyl)-3-(benzyloxymethyl)uridine-5'-aldehyde

Chemical Property of 2',3'-bis(O-tert-butyldimethylsilyl)-3-(benzyloxymethyl)uridine-5'-aldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2',3'-bis(O-tert-butyldimethylsilyl)-3-(benzyloxymethyl)uridine-5'-aldehyde

There total 4 articles about 2',3'-bis(O-tert-butyldimethylsilyl)-3-(benzyloxymethyl)uridine-5'-aldehyde 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: 98.0%

3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil (1332758-07-2) → 2',3'-bis(O-tert-butyldimethylsilyl)-3-(benzyloxymethyl)uridine-5'-aldehyde (1346620-21-0)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In acetonitrile; at 80 ℃; for 0.75h;

DOI:10.1021/jo201935w

Reference yield:

3-(benzyloxymethyl)-1-[2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil (1332758-04-9) → 2',3'-bis(O-tert-butyldimethylsilyl)-3-(benzyloxymethyl)uridine-5'-aldehyde (1346620-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / tetrahydrofuran; water / 7 h / 0 °C

1.2: pH 9

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 0.75 h / 80 °C

With trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; water; acetonitrile;

DOI:10.1021/jo201935w

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 2',3'-bis(O-tert-butyldimethylsilyl)-3-(benzyloxymethyl)uridine-5'-aldehyde (1346620-21-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C

1.2: 5 h / 0 °C

2.1: trifluoroacetic acid / tetrahydrofuran; water / 7 h / 0 °C

2.2: pH 9

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 0.75 h / 80 °C

With sodium hydride; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1021/jo201935w

upstream raw materials:

3-(benzyloxymethyl)-1-[2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil

3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil

Benzyloxymethyl chloride

2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine

Downstream raw materials:

C₄₃H₆₃N₃O₁₀Si₂

C₄₃H₆₅N₃O₁₀Si₂

C₄₃H₆₅N₃O₁₀Si₂

C₃₄H₅₅N₅O₁₀Si₂