N4-Acetyl-2'-O-methyl-cytidine

Base Information

• Chemical Name: N4-Acetyl-2'-O-methyl-cytidine
• CAS No.: 113886-71-8
• Molecular Formula: C12H17 N3 O6
• Molecular Weight: 299.28000
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00447815
• Nikkaji Number: J2.140.787I
• Wikidata: Q82266709
• Mol file: 113886-71-8.mol

Synonyms:113886-71-8;N4-ACETYL-2'-O-METHYL-CYTIDINE;Ac-2'-OMe-C;N4-Acetyl-2'-O-methylcytidine;Cytidine, N-acetyl-2'-O-methyl-;N-[1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide;N4-Acetyl-2/'-O-Methyl-cytidine;N-(1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide;Cytidine,N-acetyl-2'-O-methyl-;N4-Acetyl-2'-O-methyl cytidine;MFCD15145149;Ac-2/'-OMe-C;N4-Acetyl-2'-OMe-Cytidine;N-Acetyl-2'-O-methylcytidine;SCHEMBL3499005;DTXSID00447815;CYDFBLGNJUNSCC-QCNRFFRDSA-N;N4 -acetyl-2'-O-methyl cytidine;HG1334;AKOS015899633;AC-32177;BP-58844;BS-19249;CS-0172018;A852218;J-700206;N-(1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide;N-{1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamide

Chemical Property of N4-Acetyl-2'-O-methyl-cytidine

Chemical Property:

• PKA: 10.20±0.20(Predicted)
• PSA: 126.40000
• Density: 1.58±0.1 g/cm3(Predicted)
• LogP: -0.88320
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 299.11173527
• Heavy Atom Count: 21
• Complexity: 491

Purity/Quality:

98%, ^*data from raw suppliers

N4-Acetyl-2'-O-methylcytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=NC(=O)N(C=C1)C2C(C(C(O2)CO)O)OC
• Isomeric SMILES: CC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)OC
• Uses: N4-Acetyl-2’-O-methyl-cytidine is a useful compound in the synthesis of functionalized oligonucleotides.

Technology Process of N4-Acetyl-2'-O-methyl-cytidine

There total 6 articles about N4-Acetyl-2'-O-methyl-cytidine 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: 60.0%

N-[2-Oxo-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1,2-dihydro-pyrimidin-4-yl]-acetamide (199593-14-1) → N4-acetyl-2'-O-methyl cytidine (113886-71-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1080/07328319708006236

Reference yield:

2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine acetate (10212-28-9) → N4-acetyl-2'-O-methyl cytidine (113886-71-8)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride; MeOH / 48 h / Heating

2: 0.94 g / dimethylformamide / 20 °C

With methanol; boron trifluoride; In N,N-dimethyl-formamide; 1: Ring cleavage / 2: Acetylation;

DOI:10.1016/S0040-4020(00)00002-8

Reference yield:

acetic anhydride (108-24-7) + 2'-O-methylcytidine (2140-72-9,58970-16-4) → N4-acetyl-2'-O-methyl cytidine (113886-71-8)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0040-4020(00)00002-8

upstream raw materials:

1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol

N-(2-Oxo-1-trimethylsilanyl-1,2-dihydro-pyrimidin-4-yl)-acetamide

N-[2-Oxo-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1,2-dihydro-pyrimidin-4-yl]-acetamide

acetic anhydride

Downstream raw materials:

Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Refernces

• 1、 Reddy,Hanna, Naeem B.,Farooqui, Firdous. "Ultrafast cleavage and deprotection of oligonucleotides synthesis and use of C(Ac) derivatives". . p. 1589 - 1598. Retrieved 2007/10/03.