5'-DMTr-2'-Methseleno-Uridine

Base Information

• Chemical Name: 5'-DMTr-2'-Methseleno-Uridine
• CAS No.: 393802-82-9
• Molecular Formula: C31H32N2O7Se
• Molecular Weight: 623.564
• Mol file: 393802-82-9.mol

Synonyms:5'-DMTr-2'-Methseleno-Uridine;5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-Se-methyl-2'-selenouridine

Chemical Property of 5'-DMTr-2'-Methseleno-Uridine

Chemical Property:

• PSA: 112.01000
• LogP: 3.36160

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5'-DMTr-2'-Methseleno-Uridine

There total 6 articles about 5'-DMTr-2'-Methseleno-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: 96.0%

dimethyl diselenide (7101-31-7) + 2,2'-O-anhydro-1-<5'-O-(4,4'-dimethoxytrityl)-β-D-arabinofuranosyl>uracil (173170-12-2) → 5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methoxyuridine (393802-82-9)

Guidance literature:

dimethyl diselenide; With sodium tetrahydroborate; In tetrahydrofuran; ethanol;

2,2'-O-anhydro-1-<5'-O-(4,4'-dimethoxytrityl)-β-D-arabinofuranosyl>uracil; In tetrahydrofuran; ethanol; at 20 ℃; for 3h; Further stages.;

DOI:10.1021/ja0171097

Reference yield:

2,2'-Anhydrouridine (3736-77-4) → 5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methoxyuridine (393802-82-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / pyridine / 20 °C

2: 92 percent / sodium borohydride / tetrahydrofuran; ethanol / 2 h / 20 °C

With pyridine; sodium tetrahydroborate; In tetrahydrofuran; ethanol;

DOI:10.1021/ja038481k

Reference yield:

uridine (58-96-8) → 5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methoxyuridine (393802-82-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / diphenyl carbonate; uridine; sodium bicarbonate / dimethylformamide / 4 h / 120 °C

2: 67 percent / pyridine / 20 °C

3: 92 percent / sodium borohydride / tetrahydrofuran; ethanol / 2 h / 20 °C

With pyridine; bis(phenyl) carbonate; sodium tetrahydroborate; sodium hydrogencarbonate; uridine; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/ja038481k

upstream raw materials:

dimethyl diselenide

2,2'-O-anhydro-1-<5'-O-(4,4'-dimethoxytrityl)-β-D-arabinofuranosyl>uracil

2,2'-Anhydrouridine

uridine

Downstream raw materials:

N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-methylseleno-2'-deoxycytidine

3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine

N⁴-acetyl-3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine

2,4,6-Triisopropyl-benzenesulfonic acid 1-[(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-methylselanyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl ester

Refernces

• 1、 Du,Carrasco,Teplova,Wilds,Egli,Huang. "Internal derivatization of oligonucleotides with selenium for x-ray crystallography using MAD". . p. 24 - 25. Retrieved 2007/10/03.