5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine

Base Information

• Chemical Name: 5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine
• CAS No.: 23669-79-6
• Molecular Formula: C30H30N2O7
• Molecular Weight: 530.577
• Hs Code.: 29349990
• European Community (EC) Number: 245-814-9
• DSSTox Substance ID: DTXSID90946483
• Nikkaji Number: J242.643I
• Wikidata: Q72468687
• Mol file: 23669-79-6.mol

Synonyms:23669-79-6;5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine;C30H30N2O7;EINECS 245-814-9;1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione;2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine;5'-O-(Bis(4-methoxyphenyl)benzyl)-2'-deoxyuridine;5'-O-[Bis(4-methoxyphenyl)benzyl]-2'-deoxyuridine;1-[(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxyoxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione;2'-Deoxy-5'-O-DMT-uridine;MFCD00063410;SCHEMBL912656;DTXSID90946483;HG1169;AKOS022179908;HY-W097792;AS-70542;CS-0150434;A816833;1-[5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-hydroxy-tetrahydrofuran-2-yl]pyrimidine-2,4-dione;1-{5-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2-deoxypentofuranosyl}-4-hydroxypyrimidin-2(1H)-one

Chemical Property of 5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine

Chemical Property:

• Melting Point: 120 °C
• Refractive Index: 1.61
• PKA: 9.39±0.10(Predicted)
• PSA: 112.01000
• Density: 1.294 g/cm³
• LogP: 3.21090
• Storage Temp.: −20°C
• Solubility.: Soluble in acetonitrile at 20mg/ml
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 530.20530130
• Heavy Atom Count: 39
• Complexity: 835

Purity/Quality:

98%, ^*data from raw suppliers

5''-O-(4,4''-Dimethoxytrityl)-2’-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/22-36/37/38
• Safety Statements: 22-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OCC4C(CC(O4)N5C=CC(=O)NC5=O)O
• Isomeric SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OC[C@@H]4[C@H](C[C@@H](O4)N5C=CC(=O)NC5=O)O
• Uses: It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Technology Process of 5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine

There total 9 articles about 5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine 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: 99.0%

2'-deoxyuridine (951-78-0,63844-76-8) + 4,4'-dimethoxytrityl chloride (40615-36-9) → DMT-dU (23669-79-6)

Guidance literature:

With pyridine; for 3h; Ambient temperature;

DOI:10.1016/0968-0896(96)00156-3

Reference yield: 89.0%

2'-deoxyuridine (951-78-0,63844-76-8) + bis(4-methoxyphenyl)phenylmethylium tetrafluoroborate → DMT-dU (23669-79-6)

Guidance literature:

With lithium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; Heating;

DOI:10.1016/j.bmcl.2010.12.098

Reference yield: 65.0%

2'-deoxyuridine (951-78-0,63844-76-8) + 4,4'-dimethoxytrityl alcohol (40615-35-8) → DMT-dU (23669-79-6)

Guidance literature:

With ambelyst-15; In dichloromethane; for 3h; regioselective reaction; Reflux; Molecular sieve;

DOI:10.1080/07328303.2018.1487974

upstream raw materials:

2'-deoxyuridine

4,4'-dimethoxytrityl chloride

(MeO)2Tr-OAc

4,4'-dimethoxytrityl alcohol

Downstream raw materials:

Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester

DMT-dU-Bn

3'-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine

1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-tetrahydrofuran-2-yl]pyrimidine-2,4-dione

Refernces

Versatile strategy for oligonucleotide derivatization. Introduction of lanthanide(III) chelates to oligonucleotides

10.1021/ol016093m

2'-Deoxy-5'-O-(4,4'-dimethoxytrityl)uridine (1) is a protected nucleoside, specifically a protected deoxyuridine. The 5'-hydroxyl group is protected with a 4,4'-dimethoxytrityl (DMT) group, which is commonly used in solid phase oligonucleotide synthesis to prevent unwanted reactions at the 5' position. It serves as a starting material for the synthesis of nucleoside phosphoramidite building blocks. The DMT group can be removed later in the synthesis to allow for further functionalization. 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphoramidite is a phosphoramidite reagent used in the phosphorylation step of nucleoside phosphoramidite synthesis. It is used to convert nucleoside derivatives (2a-d) into the desired phosphoramidites (3a-d) which are then used in machine-assisted DNA synthesis. Succinic anhydride, a cyclic anhydride used for alcohol esterification, was used to convert the nucleoside derivative 2a to the corresponding succinate ester (17), which was then immobilized on a long-chain alkylamine CPG polymer support.

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