(+/-)-N⁴-benzoyl-1-[4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-cytosine

Base Information

• Chemical Name: (+/-)-N⁴-benzoyl-1-[4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-cytosine
• CAS No.: 918954-96-8
• Molecular Formula: C₂₉H₄₇N₃O₅Si₂
• Molecular Weight: 573.88
• Mol file: 918954-96-8.mol

Synonyms:(+/-)-N⁴-benzoyl-1-[4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-cytosine

Chemical Property of (+/-)-N⁴-benzoyl-1-[4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-N⁴-benzoyl-1-[4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-cytosine

There total 4 articles about (+/-)-N⁴-benzoyl-1-[4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-cytosine 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: 65.0%

(+/-)-4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl acetate (918954-93-5) + 4-N-benzoylcytosine (26661-13-2) → (+/-)-N4-benzoyl-1-[4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-cytosine (918954-96-8)

Guidance literature:

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,2-dichloro-ethane; at 20 ℃;

DOI:10.1080/15257770500379173

Reference yield:

ethyl 3,3-bis(tert-butyldimethylsilanyloxymethyl)-4-oxobutyrate (875484-14-3) → (+/-)-N4-benzoyl-1-[4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-cytosine (918954-96-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / DIBAL-H / toluene / 0.33 h / -78 °C

2: 90 percent / pyridine / 20 °C

3: 65 percent / HDMS; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 20 °C

With pyridine; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,2-dichloro-ethane; toluene;

DOI:10.1080/15257770500379173

Reference yield:

(+/-)-4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-ol (918954-92-4) → (+/-)-N4-benzoyl-1-[4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-cytosine (918954-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / 20 °C

2: 65 percent / HDMS; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 20 °C

With pyridine; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,2-dichloro-ethane;

DOI:10.1080/15257770500379173

upstream raw materials:

(+/-)-4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl acetate

4-N-benzoylcytosine

ethyl 3,3-bis(tert-butyldimethylsilanyloxymethyl)-4-oxobutyrate

(+/-)-4,4-bis-(t-butyldimethylsilyloxymethyl)tetrahydrofuran-2-ol