1β-(6-phenylpyridin-3-yl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose

Base Information

• Chemical Name: 1β-(6-phenylpyridin-3-yl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose
• CAS No.: 1315250-86-2
• Molecular Formula: C₃₄H₅₉NO₄Si₃
• Molecular Weight: 630.103
• Mol file: 1315250-86-2.mol

Synonyms:1β-(6-phenylpyridin-3-yl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose

Chemical Property of 1β-(6-phenylpyridin-3-yl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1β-(6-phenylpyridin-3-yl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose

There total 3 articles about 1β-(6-phenylpyridin-3-yl)-2,3,5-tri-O-(tert-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: 95.0%

1β-(6-bromopyridin-3-yl)-1-deoxy-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose (1315250-75-9) + phenylboronic acid (98-80-6) → 1β-(6-phenylpyridin-3-yl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose (1315250-86-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In toluene; at 110 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jo200949c

Reference yield:

(3R,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one (92512-25-9) → 1β-(6-phenylpyridin-3-yl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose (1315250-86-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / diethyl ether; hexane / 0.55 h / -78 °C

1.2: 0.22 h / -78 °C

2.1: triethylsilane / dichloromethane / 0.08 h / -10 °C

2.2: 0.08 h / -10 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / toluene / 1.5 h / 110 °C / Inert atmosphere

With triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; potassium carbonate; In diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1021/jo200949c

Reference yield:

1β-(6-bromopyridin-3-yl)-1-O-acetyl-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose (1315250-74-8) → 1β-(6-phenylpyridin-3-yl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose (1315250-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylsilane / dichloromethane / 0.08 h / -10 °C

1.2: 0.08 h / -10 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / toluene / 1.5 h / 110 °C / Inert atmosphere

With triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In dichloromethane; toluene;

DOI:10.1021/jo200949c

upstream raw materials:

1β-(6-bromopyridin-3-yl)-1-O-acetyl-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose

1β-(6-bromopyridin-3-yl)-1-deoxy-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose

phenylboronic acid

(3R,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one

Downstream raw materials:

1β-(6-phenylpyridin-3-yl)-1-deoxy-D-ribofuranose