Uridine, 3'-(bromomethyl)-3'-deoxy-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(4 -methoxyphenyl)diphenylmethyl]-

Base Information

• Chemical Name: Uridine, 3'-(bromomethyl)-3'-deoxy-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(4 -methoxyphenyl)diphenylmethyl]-
• CAS No.: 377773-04-1
• Molecular Formula: C36H43BrN2O6Si
• Molecular Weight: 707.737
• Mol file: 377773-04-1.mol

Synonyms:

Chemical Property of Uridine, 3'-(bromomethyl)-3'-deoxy-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(4 -methoxyphenyl)diphenylmethyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Uridine, 3'-(bromomethyl)-3'-deoxy-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(4 -methoxyphenyl)diphenylmethyl]-

There total 2 articles about Uridine, 3'-(bromomethyl)-3'-deoxy-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(4 -methoxyphenyl)diphenylmethyl]- 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: 73.0%

1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-hydroxymethyl-5-O-(4-methoxytriphenylmethyl)-β-D-ribo-pentofuranosyl]uracil (377773-01-8) → 1-[3-C-(bromomethyl)-2-O-(tert-butyldimethylsilyl)-3-deoxy-5-O-(4-methoxytriphenylmethyl)-β-D-ribo-pentofuranosyl]uracil (377773-04-1)

Guidance literature:

With pyridine; carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20 ℃; for 40h;

DOI:10.1081/NCN-100002562

Reference yield:

1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-methylene-5-O-(4-monomethoxytrityl)-β-D-erythro-pentofuranosyl]uracil (377773-00-7) → 1-[3-C-(bromomethyl)-2-O-(tert-butyldimethylsilyl)-3-deoxy-5-O-(4-methoxytriphenylmethyl)-β-D-ribo-pentofuranosyl]uracil (377773-04-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 9-borabicyclo[3.3.1]nonane / hexane / 20 h / 20 °C

1.2: 64 percent / NaBO₃*4H₂O / tetrahydrofuran; methanol; H₂O / 30 h / 20 °C

2.1: 73 percent / triphenylphosphine; carbon tetrabromide; pyridine / acetonitrile / 40 h / 20 °C

With pyridine; carbon tetrabromide; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; In hexane; acetonitrile;

DOI:10.1081/NCN-100002562

Reference yield: 50.0%

triethylamine carbonate (15715-58-9) + 1-[3-C-(bromomethyl)-2-O-(tert-butyldimethylsilyl)-3-deoxy-5-O-(4-methoxytriphenylmethyl)-β-D-ribo-pentofuranosyl]uracil (377773-04-1) → triethylammonium 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-5'-O-(4-methoxytriphenylmethyl)uridine 3'-C-methylenephosphinate (452310-81-5)

Guidance literature:

1-[3-C-(bromomethyl)-2-O-(tert-butyldimethylsilyl)-3-deoxy-5-O-(4-methoxytriphenylmethyl)-β-D-ribo-pentofuranosyl]uracil; With bis(trimethylsilyl)phosphonite; N-ethyl-N,N-diisopropylamine; In acetonitrile; at -42 ℃; for 8h;

triethylamine carbonate; In dichloromethane; water; at 20 ℃; Further stages.;

DOI:10.1002/1099-0690(200205)2002:9<1509::AID-EJOC1509>3.0.CO;2-X

upstream raw materials:

1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-hydroxymethyl-5-O-(4-methoxytriphenylmethyl)-β-D-ribo-pentofuranosyl]uracil

1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-methylene-5-O-(4-monomethoxytrityl)-β-D-erythro-pentofuranosyl]uracil

Downstream raw materials:

triethylammonium 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-5'-O-(4-methoxytriphenylmethyl)uridine 3'-C-methylenephosphinate