5'-O-DMT-2'-TBDMS-Uridine

Base Information

• Chemical Name: 5'-O-DMT-2'-TBDMS-Uridine
• CAS No.: 81246-80-2
• Molecular Formula: C36H44N2O8Si
• Molecular Weight: 660.839
• DSSTox Substance ID: DTXSID50451982
• Nikkaji Number: J741.053K
• Wikidata: Q82272315
• Mol file: 81246-80-2.mol

Synonyms:5'-O-DMT-2'-TBDMS-Uridine;81246-80-2;1-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione;1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione;2'-O-(tert-Butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)uridine;SCHEMBL1582059;DTXSID50451982;MFCD00135726;AKOS015999127;HY-W102322;AC-32207;AS-10167;PD158436;CS-0154964;2'-O-tertButyldimethylsilyl-5'-O-DMT-uridine;C76600;3'-O-tert-Butyldimethylsilyl-5'-O-DMT-uridine;A848822;J-700111;J-700365;2'-O-tert-Butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)uridine;5'-O-(4,4'-Dimethoxytrityl) 2'-O-[(1,1-dimethylethyl)-dimethylsilyl]-uridine;1-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-((tert-butyldmethylsilyl)oxy)-4-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione;1-[(2R,3R,4R,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-3-[(tert-butyldimethylsilyl)oxy]-4-hydroxyoxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Chemical Property of 5'-O-DMT-2'-TBDMS-Uridine

Chemical Property:

• PSA: 121.24000
• LogP: 5.21120
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 660.28669290
• Heavy Atom Count: 47
• Complexity: 1070

Purity/Quality:

98%, ^*data from raw suppliers

5''-O-DMT-2''-TBDMS-Uridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1C(C(OC1N2C=CC(=O)NC2=O)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)O
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)O
• Uses: 5''-O-DMT-2''-TBDMS-Uridine (cas# 81246-80-2) is a nucleoside and has been used in the prepartion of pseudorotaxane architectures. It has also been able to undergo microwave-assisted phosphitylation in the preparation of nucleoside phosphoramidites.

Technology Process of 5'-O-DMT-2'-TBDMS-Uridine

There total 12 articles about 5'-O-DMT-2'-TBDMS-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: 93.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 5'-dimethoxytrityluridine (81246-79-9) → 5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl uridine (81246-80-2)

Guidance literature:

With (2R,4S)-3-((R)-cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl)-4-isopropyl-2-methoxyoxazolidine; N,N-diisopropylethylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 24h; Reagent/catalyst; Concentration; Inert atmosphere;

DOI:10.1021/ol402023c

Reference yield: 90.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-(tert-butyldimethylsilyl)uridine (54925-71-2) → 5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl uridine (81246-80-2)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1081/NCN-120022724

Reference yield: 70.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 5'-dimethoxytrityluridine (81246-79-9) → 5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3'-O-[dimethyl(tert-butyl)silyl]uridine (81246-81-3) + 5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl uridine (81246-80-2)

Guidance literature:

With silver perchlorate; 1,4-diaza-bicyclo[2.2.2]octane; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(01)92470-0

upstream raw materials:

tert-butyldimethylsilyl chloride

5'-dimethoxytrityluridine

tert-butyldimethylsilyl nitrate

4,4'-dimethoxytrityl chloride

Downstream raw materials:

5'-dimethoxytrityl 2'-tert-butyldimethyl silyl uridine 3'-p-chlorophenyl β-cyanoethyl phosphotriester

4-(1,2,4-triazol-1-yl)-1-<5'-O-(dimethoxytrityl)-3'-O-((p-chlorophenoxy)(2-cyanoethoxy)phosphoryl)-2'-O-(tert-butyldimetylsilyl)-β-D-ribofuranosyl>pyrimidin-2-(1H)-one

4-tetrazolo-1-(β-D-5'-dimethoxytrityl-2'-tert-butyldimethyl silyl ribofuranosyl)-2(1H)-pyrimidinone 3'-p-chlorophenyl β-cyanoethyl phosphotriester

5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridine 3'-O-(2-cyanoethyl N,N-diethylphosphoramidite)

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