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

Base Information

• Chemical Name: (Z)-3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-iodo-β-D-ribopentofuranosyl]uracil
• CAS No.: 1332757-98-8
• Molecular Formula: C₂₉H₄₅IN₂O₆Si₂
• Molecular Weight: 700.762
• Mol file: 1332757-98-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (Z)-3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-iodo-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: 79.0%

3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-β-D-ribopentofuranosyl]uracil (1332758-11-8) → (Z)-3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-iodo-β-D-ribopentofuranosyl]uracil (1332757-98-8)

Guidance literature:

With iodonium di(2,4,6-collidinium) triflate; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol202124b

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (Z)-3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-iodo-β-D-ribopentofuranosyl]uracil (1332757-98-8)

Guidance literature:

Multi-step reaction with 5 steps

1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

2: trifluoroacetic acid / tetrahydrofuran; water / 7 h / 0 °C / Inert atmosphere

3: pyridine; iodine; triphenylphosphine / 1,4-dioxane / 16 h / 20 °C / Inert atmosphere

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0 - 20 °C / Inert atmosphere

5: iodonium di(2,4,6-collidinium) triflate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With pyridine; iodonium di(2,4,6-collidinium) triflate; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol202124b

Reference yield:

3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil (1332758-07-2) → (Z)-3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-iodo-β-D-ribopentofuranosyl]uracil (1332757-98-8)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; iodine; triphenylphosphine / 1,4-dioxane / 16 h / 20 °C / Inert atmosphere

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

3: iodonium di(2,4,6-collidinium) triflate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With pyridine; iodonium di(2,4,6-collidinium) triflate; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1021/ol202124b

upstream raw materials:

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

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

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

Downstream raw materials:

C₆₁H₉₃N₉O₁₄Si₂

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

N³-benzyloxymethyluracil

C₅₀H₇₆N₆O₁₂Si₂