3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-β-D-ribopentofuranosyl]uracil

Base Information

• Chemical Name: 3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-β-D-ribopentofuranosyl]uracil
• CAS No.: 1332758-18-5
• Molecular Formula: C₂₃H₃₂N₂O₅Si
• Molecular Weight: 444.603
• Mol file: 1332758-18-5.mol

Synonyms:3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-β-D-ribopentofuranosyl]uracil

Chemical Property of 3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-β-D-ribopentofuranosyl]uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-β-D-ribopentofuranosyl]uracil

There total 5 articles about 3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-β-D-ribopentofuranosyl]uracil 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: 93.0%

3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil (1332758-17-4) → 3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-β-D-ribopentofuranosyl]uracil (1332758-18-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol202124b

Reference yield:

3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-5-O-(triphenylmethyl)-β-D-ribopentofuranosyl]uracil (1332758-15-2) → 3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-β-D-ribopentofuranosyl]uracil (1332758-18-5)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / water / 3 h / 60 °C

2: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 3.17 h / 0 - 20 °C / Inert atmosphere

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; iodine; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; water; acetonitrile;

DOI:10.1021/ol202124b

Reference yield:

3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-ribo-pentofuranosyl]uracil (1332758-16-3) → 3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-β-D-ribopentofuranosyl]uracil (1332758-18-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 3.17 h / 0 - 20 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ol202124b

upstream raw materials:

3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-5-O-(triphenylmethyl)-β-D-ribopentofuranosyl]uracil

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

3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

Benzyloxymethyl chloride

Downstream raw materials:

(Z)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

C₂₃H₃₁IN₂O₅Si

(E)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

C₅₅H₇₉N₉O₁₃Si