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

Base Information

• Chemical Name: 1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose
• CAS No.: 1407180-88-4
• Molecular Formula: C₃₀H₅₇BrO₄Si₃
• Molecular Weight: 645.941
• Mol file: 1407180-88-4.mol

Synonyms:1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose

Chemical Property of 1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose

There total 1 articles about 1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-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: 36.0%

1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose (1407180-87-3) → 1β-(2-bromobenzyl)-2,5-di-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose (1407180-89-5) + 1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose (1407180-88-4) + 1β-(2-bromobenzyl)-3,5-di-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose (1407180-90-8)

Guidance literature:

1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose; With triethylsilane; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.0833333h; Overall yield = 76 %; Overall yield = 4 g; Inert atmosphere;

DOI:10.1002/ejoc.201200819

Reference yield: 91.0%

1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose (1407180-88-4) + trimethylaluminum (75-24-1) → 2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-1β-(2-methylbenzyl)-D-ribofuranose (1407180-92-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; toluene; at 70 ℃; for 24h; Inert atmosphere;

DOI:10.1002/ejoc.201200819

Reference yield: 87.0%

1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose (1407180-88-4) + phenylboronic acid (98-80-6) → 2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-1β-(2-phenylbenzyl)-D-ribofuranose (1407180-93-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In toluene; at 90 ℃; for 12h; Inert atmosphere;

DOI:10.1002/ejoc.201200819

upstream raw materials:

1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-D-ribofuranose

Downstream raw materials:

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

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

1-deoxy-1β-(2-phenylbenzyl)-D-ribofuranose

2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-1β-[2-(dimethylamino)benzyl]-D-ribofuranose