rU Phosphoramidite

Base Information

• Chemical Name: rU Phosphoramidite
• CAS No.: 118362-03-1
• Molecular Formula: C₄₅H₆₁N₄O₉PSi
• Molecular Weight: 861.06
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID50447507
• Nikkaji Number: J404.978K
• Mol file: 118362-03-1.mol

Synonyms:rU Phosphoramidite;118362-03-1;(2R,3R,4R,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite;3-[[(2R,3R,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile;DMT-2'O-TBDMS-rU Phosphoramidite;DMT-2'O-TBDMS-rU Phosphoramidite, configured for ABI;C45H61N4O9PSi;DMT-2'O-TBDMS-rU Phosphoramidite, configured for MerMade;rUPhosphoramidite;DMT-2'O-TBDMS-rU Phosphoramidite, configured for ??KTA(R) and OligoPilot(R);SCHEMBL667356;DTXSID50447507;DMT-2'O-TBDMS-rU Pharmadite(R);AKOS015999123;144490-31-3;AC-32374;CS-0100730;2'-O-(tert-Butyldimethylsilyl)-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)uridine;5/'-O-(4,4-Dimethoxytrityl)-2/'-O-[(tert-butyl)dimethylsilyl]uridine-3/'-(2-cyanoethyl-N,N-diisoprop

Chemical Property of rU Phosphoramidite

Chemical Property:

• PKA: 9.39±0.10(Predicted)
• PSA: 160.09000
• LogP: 8.51148
• Storage Temp.: ?20°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 20
• Exact Mass: 860.39454307
• Heavy Atom Count: 60
• Complexity: 1430

Purity/Quality:

98% ^*data from raw suppliers

DMT-2′O-TBDMS-rU Phosphoramidite ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1O[Si](C)(C)C(C)(C)C)N2C=CC(=O)NC2=O)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC
• Isomeric SMILES: CC(C)N(C(C)C)P(OCCC#N)O[C@@H]1[C@H](O[C@H]([C@@H]1O[Si](C)(C)C(C)(C)C)N2C=CC(=O)NC2=O)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC
• Uses: DMT-2′O-TBDMS-rU Phosphoramidite was used in study of efficient enzyme-free copying of all four nucleobases templated by immobilized RNA.

Technology Process of rU Phosphoramidite

There total 4 articles about rU Phosphoramidite 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: 84.0%

5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl uridine (81246-80-2) + N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridine-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (144490-31-3,118362-03-1,131349-31-0,131349-37-6)

Guidance literature:

With 1H-tetrazole; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2010.07.068

Reference yield: 83.0%

→ (2R,3R,4R,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)met hoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl(2-cyanoethyl)diisopropylphosphoramidite (121058-88-6) + 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridine-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (144490-31-3,118362-03-1,131349-31-0,131349-37-6)

Guidance literature:

Reference yield: 82.0%

5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl uridine (81246-80-2) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridine-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (144490-31-3,118362-03-1,131349-31-0,131349-37-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 18h;

DOI:10.1021/jo00015a010

upstream raw materials:

5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl uridine

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridin-3'-yl H-phosphonate

C₆₅H₇₅N₄O₁₂PSi

5'-O-((2-cyanoethoxy)-(5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridin-3'-yl)phosphoryl)-2'-O-(tert-butyldimethylsilyl)uridine

Refernces

• 1、 Ching, Shi Min,Tan, Wan Jun,Chua, Kim Lee,Lam, Yulin. "Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase". experimental part. p. 6657 - 6665. Retrieved 2010/10/21.
• 2、 -. "Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives". . . Retrieved 2008/06/13.