1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-((o-nitrophenyl)seleno)propyl)uridine

Base Information

• Chemical Name: 1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-((o-nitrophenyl)seleno)propyl)uridine
• CAS No.: 149204-12-6
• Molecular Formula: C₃₀H₄₅N₃O₁₀SeSi
• Molecular Weight: 714.747
• Mol file: 149204-12-6.mol

Synonyms:1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-((o-nitrophenyl)seleno)propyl)uridine

Chemical Property of 1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-((o-nitrophenyl)seleno)propyl)uridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-((o-nitrophenyl)seleno)propyl)uridine

There total 7 articles about 1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-((o-nitrophenyl)seleno)propyl)uridine 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: 86.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + 1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-hydroxypropyl)uridine (149204-10-4) → 1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-((o-nitrophenyl)seleno)propyl)uridine (149204-12-6)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; for 1h;

DOI:10.1021/jo00062a014

Reference yield:

2',3'-O-isopropylideneuridine (362-43-6) → 1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-((o-nitrophenyl)seleno)propyl)uridine (149204-12-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) LDA / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 90 h

2: 74 percent / aq. TFA / acetone

3: 82 percent / p-TsOH / acetone / Heating

4: 93 percent / NEt₃, DMAP / dimethylformamide

6: 1) NaBH₄, 2) NH₄Cl / 1a) MeOH, 0 deg C, 10 min, 1b) r.t., 20 min, 2a) 0 deg C, 10 min, 2b) r.t., 20 min

7: 86 percent / (n-Bu)3P / tetrahydrofuran / 1 h

With dmap; sodium tetrahydroborate; tributylphosphine; ammonium chloride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00062a014

Reference yield:

1-(2',3'-O-isopropylideneurid-6-yl)-4-butyraldehyde dimethyl acetal (126740-09-8) → 1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-((o-nitrophenyl)seleno)propyl)uridine (149204-12-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / aq. TFA / acetone

2: 82 percent / p-TsOH / acetone / Heating

3: 93 percent / NEt₃, DMAP / dimethylformamide

5: 1) NaBH₄, 2) NH₄Cl / 1a) MeOH, 0 deg C, 10 min, 1b) r.t., 20 min, 2a) 0 deg C, 10 min, 2b) r.t., 20 min

6: 86 percent / (n-Bu)3P / tetrahydrofuran / 1 h

With dmap; sodium tetrahydroborate; tributylphosphine; ammonium chloride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00062a014

upstream raw materials:

ortho-nitrophenyl selenocyanate

1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl))-5-(dimethoxymethyl)-6-(3-hydroxypropyl)uridine

2',3'-O-isopropylideneuridine

<1H,3H>-1-(2',3'-O-isopropylidene-β-D-ribofuranosyl)-7,8-dihydroquinazoline-2,4-dione