1-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
• CAS No.: 103285-22-9
• Molecular Formula: C31H32 N2 O8
• Molecular Weight: 560.604
• DSSTox Substance ID: DTXSID30452856
• Nikkaji Number: J1.368.141D
• Wikidata: Q82273714
• Mol file: 103285-22-9.mol

Synonyms:103285-22-9;5'-O-(4,4'-Dimethoxytrityl)-2'-O-methyluridine;1-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione;1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-methoxyoxolan-2-yl]pyrimidine-2,4-dione;5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-O-methyl-uridine;5'-O-DMT-2'-O-METHYL-URIDINE;5'-O-DMT-2'-O-methyluridine;5'-o-(bis(4-methoxyphenyl)phenylmethyl)-2'-o-methyl-uridine;MFCD00274123;SCHEMBL6284695;DTXSID30452856;MFDHAVFJDSRPKC-YXINZVNLSA-N;C31H32N2O8;Uridine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-methyl-;5'-O-DMT-2'-O-methyl-D-uridine;HG1364;AC-32218;AS-66923;A848858;J-700122;5'-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2'-O-methyluridine;1-((2S,3S,4S,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxy-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione;1-[(2R,3R,4R,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxy-3-methoxyoxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Chemical Property of 1-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Chemical Property:

• PKA: 9.39±0.10(Predicted)
• PSA: 121.24000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 2.83580
• Storage Temp.: Store dry at 2-8°C
• Solubility.: Soluble in acetonitrile
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 560.21586598
• Heavy Atom Count: 41
• Complexity: 884

Purity/Quality:

98%, ^*data from raw suppliers

5'- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(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: CO[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-(Dimethoxytrityl)-2’-O-methyluridine is a potential therapeutic agent. Also, it is a reagent used in the synthesis of 2’-modified-4’-thioRNA.

Technology Process of 1-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

There total 8 articles about 1-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 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: 90.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-methyluridine (2140-76-3) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyluridine (103285-22-9)

Guidance literature:

With pyridine; for 0.75h; Inert atmosphere;

DOI:10.1007/s00706-012-0881-7

Reference yield: 90.0%

→ 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyluridine (103285-22-9)

Guidance literature:

Reference yield: 74.0%

N-(1-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-methoxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-2-(4-tert-butyl-phenoxy)-acetamide → 5'-O-(dimethoxytrityl)-3'-O-methyluridine + 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyluridine (103285-22-9)

Guidance literature:

With lithium hydroxide; In methanol; water; for 6h; Yields of byproduct given; Heating;

DOI:10.1016/0040-4039(95)00435-F

upstream raw materials:

diazomethane

5'-dimethoxytrityluridine

4,4'-dimethoxytrityl chloride

2'-O-methyluridine

Downstream raw materials:

C₃₇H₄₆N₂O₈Si

C₃₈H₄₈N₃O₈P

5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2'-O-methyl-3'-O-(4-oxopentanoyl)uridine

Refernces

• 1、 Büttner, Lea,Seikowski, Jan,Wawrzyniak, Katarzyna,Ochmann, Anne,H?bartner, Claudia. "Synthesis of spin-labeled riboswitch RNAs using convertible nucleosides and DNA-catalyzed RNA ligation". . p. 6171 - 6180. Retrieved 2013/10/21.
• 2、 -. "Method of preparation of known and novel 2'-modified nucleosides by intramolecular nucleophilic displacement". . . Retrieved 2008/06/13.