N-(1-((2R,4S,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Base Information

• Chemical Name: N-(1-((2R,4S,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide
• CAS No.: 100898-63-3
• Molecular Formula: C32H33 N3 O7
• Molecular Weight: 571.63
• European Community (EC) Number: 691-405-7
• Nikkaji Number: J789.344B
• Mol file: 100898-63-3.mol

Synonyms:100898-63-3;5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE;N-Acetyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-cytidine;N-(1-((2R,4S,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide;5'-O-DMT-N4-Ac-dC;N4-Acetyl-2'-deoxy-5'-O-DMT-cytidine;Cytidine, N-acetyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-;N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide;DMT-NAC-DC;N-Acetyl-5'-DMTdeoxycytidine;N-Acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine;N-Acetyl-5'-O-[bis(4-methoxyphenyl)-phenylmethyl]-2'-deoxy-cytidine;SCHEMBL20596260;MFCD05663669;5'-DMT-N4-acetyl-2'-deoxycytidine;HY-W077279;5'-O-DMT-N4-Acetyl-2'-Deoxycytidine;BP-58858;BS-19069;PD158421;CS-0120007;D94439;A852149;J-700203;N4-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine;N-(1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Chemical Property of N-(1-((2R,4S,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Chemical Property:

• PKA: 10.28±0.20(Predicted)
• PSA: 121.14000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 3.94900
• Storage Temp.: Store dry at 2-8°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 571.23185040
• Heavy Atom Count: 42
• Complexity: 957

Purity/Quality:

98%, ^*data from raw suppliers

5''-O-(4,4''-Dimethoxytrityl)-N4-acetyl-2''-deoxycytidine ^*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)C2CC(C(O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)O
• Isomeric SMILES: CC(=O)NC1=NC(=O)N(C=C1)[C@H]2C[C@@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)O

Technology Process of N-(1-((2R,4S,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

There total 4 articles about N-(1-((2R,4S,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide 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: 85.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N4-acetyl-2'-deoxycytidine (32909-05-0) → 5’-O-(4,4’dimethoxytrityl)-N4-(acetyl)-2'-deoxycytidine (100898-63-3)

Guidance literature:

With pyridine;

DOI:10.1080/07328319708006236

Reference yield: 46.0%

C23H19F3O4 + N4-acetyl-2'-deoxycytidine (32909-05-0) → 5’-O-(4,4’dimethoxytrityl)-N4-(acetyl)-2'-deoxycytidine (100898-63-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.tetlet.2016.07.062

Reference yield:

2'-Deoxycytidine (951-77-9) → 5’-O-(4,4’dimethoxytrityl)-N4-(acetyl)-2'-deoxycytidine (100898-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / dimethylformamide

2: 85 percent / pyridine

With pyridine; In N,N-dimethyl-formamide;

DOI:10.1080/07328319708006236

upstream raw materials:

4,4'-dimethoxytrityl chloride

N⁴-acetyl-2'-deoxycytidine

2'-Deoxycytidine

4,4'-dimethoxytrityl alcohol

Downstream raw materials:

Acetic acid (2R,3S,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl 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.
• 2、 Whitfield,Douglas,Tang,Csizmadia,Pang,Moolten,Krepinsky. "Differential reactivity of carbohydrate hydroxyls in glycosylations. II. The likely role of intramolecular hydrogen bonding on glycosylation reactions. Galactosylation of nucleoside 5'-hydroxyls for the syntheses of novel potential anticancer agents". . p. 2225 - 2238. Retrieved 2007/10/02.