3-benzoyl-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hex-1-ynyl-6-iodo-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 3-benzoyl-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hex-1-ynyl-6-iodo-1H-pyrimidine-2,4-dione
• CAS No.: 319455-52-2
• Molecular Formula: C₃₁H₄₁IN₂O₇Si
• Molecular Weight: 708.666
• Mol file: 319455-52-2.mol

Synonyms:

Chemical Property of 3-benzoyl-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hex-1-ynyl-6-iodo-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-benzoyl-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hex-1-ynyl-6-iodo-1H-pyrimidine-2,4-dione

There total 4 articles about 3-benzoyl-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hex-1-ynyl-6-iodo-1H-pyrimidine-2,4-dione 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: 71.0%

benzoyl chloride (98-88-4) + 1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hex-1-ynyl-6-iodo-1H-pyrimidine-2,4-dione (319455-50-0) → 3-benzoyl-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hex-1-ynyl-6-iodo-1H-pyrimidine-2,4-dione (319455-52-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine;

DOI:10.1016/S0040-4039(00)01566-5

Reference yield:

hex-1-yne (693-02-7) → 3-benzoyl-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hex-1-ynyl-6-iodo-1H-pyrimidine-2,4-dione (319455-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / Pd⁽⁰⁾; Cu(I)

2: 74 percent / LDA; I₂ / -78 °C

3: 71 percent / (iPr)2NEt

With iodine; copper; palladium; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; 1: Sonogashira coupling / 2: Iodination / 3: Acylation;

DOI:10.1016/S0040-4039(00)01566-5

Reference yield:

5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneuridine (184238-58-2) → 3-benzoyl-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hex-1-ynyl-6-iodo-1H-pyrimidine-2,4-dione (319455-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / Pd⁽⁰⁾; Cu(I)

2: 74 percent / LDA; I₂ / -78 °C

3: 71 percent / (iPr)2NEt

With iodine; copper; palladium; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; 1: Sonogashira coupling / 2: Iodination / 3: Acylation;

DOI:10.1016/S0040-4039(00)01566-5

upstream raw materials:

benzoyl chloride

1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hex-1-ynyl-6-iodo-1H-pyrimidine-2,4-dione

hex-1-yne

5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneuridine