5'-O-(Methoxymethyl)-2',3'-O-(1-methylethylidene)-6-(2-phenylethynyl)uridine

Base Information

• Chemical Name: 5'-O-(Methoxymethyl)-2',3'-O-(1-methylethylidene)-6-(2-phenylethynyl)uridine
• CAS No.: 105967-12-2
• Molecular Formula: C22H24N2O7
• Molecular Weight: 428.442
• DSSTox Substance ID: DTXSID501141553
• Mol file: 105967-12-2.mol

Synonyms:DTXSID501141553;5'-O-(Methoxymethyl)-2',3'-O-(1-methylethylidene)-6-(2-phenylethynyl)uridine;105967-12-2

Chemical Property of 5'-O-(Methoxymethyl)-2',3'-O-(1-methylethylidene)-6-(2-phenylethynyl)uridine

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 428.15835111
• Heavy Atom Count: 31
• Complexity: 805

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)N3C(=CC(=O)NC3=O)C#CC4=CC=CC=C4)COCOC)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C(=CC(=O)NC3=O)C#CC4=CC=CC=C4)COCOC)C

Technology Process of 5'-O-(Methoxymethyl)-2',3'-O-(1-methylethylidene)-6-(2-phenylethynyl)uridine

There total 3 articles about 5'-O-(Methoxymethyl)-2',3'-O-(1-methylethylidene)-6-(2-phenylethynyl)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: 71.0%

phenylacetylene (536-74-3) + 6-iodo-uridine (105967-11-1) → 2',3'-O-isopropylidene-5'-O-methoxymethyl-6-<2-(phenyl)ethynyl>uridine (105967-12-2)

Guidance literature:

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In triethylamine; at 60 ℃; for 2h;

Reference yield: 70.0%

1-iodo-2-phenylethyne (932-88-7) + 6-Tributylstannyl-2',3'-isopropylidene-5'-O-methoxymethyluridine → 2',3'-O-isopropylidene-5'-O-methoxymethyl-6-<2-(phenyl)ethynyl>uridine (105967-12-2)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)86332-8

Reference yield:

6-iodo-2',3'-O-isopropylidene-5'-O-methoxymethyluridine (98854-10-5) → 2',3'-O-isopropylidene-5'-O-methoxymethyl-6-<2-(phenyl)ethynyl>uridine (105967-12-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 50percent TFA / 6 h / Ambient temperature

2: 71 percent / Pd(Ph₃P)2Cl₂, CuI / triethylamine / 2 h / 60 °C

With trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In triethylamine;

upstream raw materials:

1-iodo-2-phenylethyne

phenylacetylene

6-iodo-uridine

6-iodo-2',3'-O-isopropylidene-5'-O-methoxymethyluridine

Downstream raw materials:

6-(2-phenyl)ethynyluridine