3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-bromo-β-D-ribopentofuranosyl]uracil

Base Information

• Chemical Name: 3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-bromo-β-D-ribopentofuranosyl]uracil
• CAS No.: 1354938-95-6
• Molecular Formula: C₂₉H₄₅BrN₂O₆Si₂
• Molecular Weight: 653.761
• Mol file: 1354938-95-6.mol

Synonyms:

Chemical Property of 3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-bromo-β-D-ribopentofuranosyl]uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-bromo-β-D-ribopentofuranosyl]uracil

There total 2 articles about 3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-bromo-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:

3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-phenylthio-β-D-ribopentofuranosyl]uracil (1354938-99-0) → 3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-bromo-β-D-ribopentofuranosyl]uracil (1354938-95-6)

Guidance literature:

3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-phenylthio-β-D-ribopentofuranosyl]uracil; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; N-ethyl-N,N-diisopropylamine; In toluene; for 6h; Inert atmosphere; Reflux;

With N-Bromosuccinimide; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo202159q

Reference yield:

C35H51ClN2O6SSi2 → 3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-bromo-β-D-ribopentofuranosyl]uracil (1354938-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / Reflux; Inert atmosphere

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; N-ethyl-N,N-diisopropylamine / toluene / 6 h / Inert atmosphere; Reflux

2.2: 2 h / 20 °C / Inert atmosphere

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; 2.1: Barton-McCombie deoxygenation;

DOI:10.1021/jo202159q

Reference yield: 19.0%

3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-bromo-β-D-ribopentofuranosyl]uracil (1354938-95-6) → 3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-β-D-ribopentofuranosyl]uracil (1332758-11-8)

Guidance literature:

With palladium diacetate; benzamide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100 ℃;

DOI:10.1021/jo202159q

upstream raw materials:

3-(benzyloxymethyl)-1-[(Z)-2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-phenylthio-β-D-ribopentofuranosyl]uracil

Downstream raw materials:

3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-β-D-ribopentofuranosyl]uracil

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

C₃₆H₅₁N₃O₇Si₂

C₃₆H₅₈N₄O₉Si₂