1β-(6-phenylpyridin-3-yl)-1,2-dideoxy-3,5-di-O-(t-butyldimethylsilyl)-D-ribofuranose

Base Information

• Chemical Name: 1β-(6-phenylpyridin-3-yl)-1,2-dideoxy-3,5-di-O-(t-butyldimethylsilyl)-D-ribofuranose
• CAS No.: 950830-63-4
• Molecular Formula: C₂₈H₄₅NO₃Si₂
• Molecular Weight: 499.841
• Mol file: 950830-63-4.mol

Synonyms:1β-(6-phenylpyridin-3-yl)-1,2-dideoxy-3,5-di-O-(t-butyldimethylsilyl)-D-ribofuranose

Chemical Property of 1β-(6-phenylpyridin-3-yl)-1,2-dideoxy-3,5-di-O-(t-butyldimethylsilyl)-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1β-(6-phenylpyridin-3-yl)-1,2-dideoxy-3,5-di-O-(t-butyldimethylsilyl)-D-ribofuranose

There total 6 articles about 1β-(6-phenylpyridin-3-yl)-1,2-dideoxy-3,5-di-O-(t-butyldimethylsilyl)-D-ribofuranose 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: 98.0%

6-bromo-3-[3,5-bis(tert-butyldimethylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]pyridine + phenylboronic acid (98-80-6) → 1β-(6-phenylpyridin-3-yl)-1,2-dideoxy-3,5-di-O-(t-butyldimethylsilyl)-D-ribofuranose (950830-63-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In toluene; at 110 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.201705797

Reference yield: 60.0%

1β-(6-chloropyridin-3-yl)-1,2-dideoxy-3,5-di-O-(tert-butyldimethylsilyl)-D-ribofuranose (950830-41-8) + phenylboronic acid (98-80-6) → 1β-(6-phenylpyridin-3-yl)-1,2-dideoxy-3,5-di-O-(t-butyldimethylsilyl)-D-ribofuranose (950830-63-4)

Guidance literature:

With potassium fluoride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; at 60 ℃; for 72h;

DOI:10.1021/jo0709504

Reference yield:

C16H24O3SiClN (950830-45-2) → 1β-(6-phenylpyridin-3-yl)-1,2-dideoxy-3,5-di-O-(t-butyldimethylsilyl)-D-ribofuranose (950830-63-4)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N*HF / tetrahydrofuran / 0.08 h / 20 °C

2: 161 mg / NaBH(OAc)3; acetic acid / acetonitrile / 0.08 h / 0 °C

3: 73 percent / imidazole / dimethylformamide / 0 - 20 °C

4: 60 percent / KF; P(t-Bu)3*HBF₃ / Pd₂(dba)3 / tetrahydrofuran / 72 h / 60 °C

With 1H-imidazole; potassium fluoride; sodium tris(acetoxy)borohydride; acetic acid; triethylamine hydrofluoride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 4: Suzuki coupling;

DOI:10.1021/jo0709504

upstream raw materials:

1β-(6-chloropyridin-3-yl)-1,2-dideoxy-3,5-di-O-(tert-butyldimethylsilyl)-D-ribofuranose

phenylboronic acid

1β-(6-chloropyridin-3-yl)-1,2-dideoxy-D-ribofuranose

C₁₆H₂₄O₃SiClN