N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-Cytidine

Base Information

• Chemical Name: N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-Cytidine
• CAS No.: 81246-78-8
• Molecular Formula: C43H49N3O8Si
• Molecular Weight: 763.95
• DSSTox Substance ID: DTXSID901115566
• Mol file: 81246-78-8.mol

Synonyms:81246-78-8;N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-Cytidine;DTXSID901115566;AC-32214;N-[1-[(2R,3R,4S,5R)-5-[[Bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide;N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]cytidine

Chemical Property of N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-Cytidine

Chemical Property:

• PSA: 130.37000
• LogP: 7.24320
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 14
• Exact Mass: 763.32889206
• Heavy Atom Count: 55
• Complexity: 1320

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1C(OC(C1O)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC

Technology Process of N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-Cytidine

There total 3 articles about N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-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: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 4-N-benzoyl-1-(5-O-dimethoxytrityl-β-D-ribofuranosyl)cytosine (81246-76-6,87418-76-6,129666-73-5) → 5'-dimethoxytrityl 3'-tert-butyldimethyl silyl N-benzoylcytidine (81246-78-8) + 5’-O-(1,1-bis(4-methoxyphenyl)-1-phenylmethyl)-2’-O-tert-butyldimethylsilylcytidine (129666-74-6,81256-87-3)

Guidance literature:

With silver nitrate; 1,4-diaza-bicyclo[2.2.2]octane; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/S0040-4039(01)92470-0

Reference yield: 15.0%

C43H49N3O7SSi (1329052-02-9) → C43H49N3O7Si (1329052-05-2) + 5'-dimethoxytrityl 3'-tert-butyldimethyl silyl N-benzoylcytidine (81246-78-8)

Guidance literature:

With tert.-butylhydroperoxide; In toluene; for 0.0833333h;

DOI:10.1016/j.tetlet.2011.06.078

Reference yield: 8.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 4-N-benzoyl-1-(5-O-dimethoxytrityl-β-D-ribofuranosyl)cytosine (81246-76-6,87418-76-6,129666-73-5) → 5'-dimethoxytrityl 3'-tert-butyldimethyl silyl N-benzoylcytidine (81246-78-8) + 5’-O-(1,1-bis(4-methoxyphenyl)-1-phenylmethyl)-2’-O-tert-butyldimethylsilylcytidine (129666-74-6,81256-87-3) + 5'-O-(dimethoxytrityl)-2',3'-O-bis(tert-butyldimetylsilyl)-N4-benzoylcytidine (81246-77-7)

Guidance literature:

With 1H-imidazole; In pyridine; for 4h; Ambient temperature;

DOI:10.1139/v82-021

upstream raw materials:

tert-butyldimethylsilyl chloride

4-N-benzoyl-1-(5-O-dimethoxytrityl-β-D-ribofuranosyl)cytosine

C₄₃H₄₉N₃O₇SSi

Downstream raw materials:

Phosphoric acid (2R,3R,4R,5R)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester; compound with triethyl-amine

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