N4-Benzoyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)cytidine

Base Information

• Chemical Name: N4-Benzoyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)cytidine
• CAS No.: 69304-43-4
• Molecular Formula: C₂₈H₄₃N₃O₇Si₂
• Molecular Weight: 589.836
• DSSTox Substance ID: DTXSID70434772
• Nikkaji Number: J1.381.145H
• Wikidata: Q82249274
• Mol file: 69304-43-4.mol

Synonyms:69304-43-4;N4-Benzoyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)cytidine;N-(1-((6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide;N-[1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxopyrimidin-4-yl]benzamide;N-Benzoyl-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-Cytidine;SCHEMBL6365808;DTXSID70434772;1172994-45-4;3',5'-TIPS-N4-Benzoyl-cytidine;STL578341;AKOS030627053;CS-15646;B3631;CS-0008586;J-700219;N-Benzoyl-3'-O,5'-O-[oxybis(diisopropylsilanediyl)]cytidine;N-{1-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetra(propan-2-yl)tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}benzamide

Chemical Property of N4-Benzoyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)cytidine

Chemical Property:

• Melting Point: 101°C(lit.)
• PKA: 8.61±0.20(Predicted)
• Density: 1.23±0.1 g/cm3(Predicted)
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 589.26395379
• Heavy Atom Count: 40
• Complexity: 980

Purity/Quality:

98%,99%, ^*data from raw suppliers

N4-Benzoyl-3'',5''-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)cytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)[Si]1(OCC2C(C(C(O2)N3C=CC(=NC3=O)NC(=O)C4=CC=CC=C4)O)O[Si](O1)(C(C)C)C(C)C)C(C)C
• Isomeric SMILES: CC(C)[Si]1(OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=NC3=O)NC(=O)C4=CC=CC=C4)O)O[Si](O1)(C(C)C)C(C)C)C(C)C
• Uses: N4-Benzoyl-3'',5''-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)cytidine (cas# 69304-43-4) is a useful chiral building block used in the preparation of mannosylated oligoribonucleotides.

Technology Process of N4-Benzoyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)cytidine

There total 12 articles about N4-Benzoyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)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: 94.0%

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + N4-benzoylcytidine (13089-48-0) → 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine (69304-43-4)

Guidance literature:

In pyridine;

DOI:10.1002/hlca.200790034

Reference yield: 86.0%

1,1,3,3-dichlorotetraisopropyldisiloxane + N4-benzoylcytidine (13089-48-0) → 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine (69304-43-4)

Guidance literature:

In pyridine; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; ethyl acetate;

Reference yield: 83.6%

1,1,3,3-tetraisopropyldisiloxane (18043-71-5) + N4-benzoylcytidine (13089-48-0) → 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine (69304-43-4)

Guidance literature:

With pyridine; at 0 ℃; for 1h; Inert atmosphere;

upstream raw materials:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

N₄-benzoylcytidine

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

benzoyl chloride

Downstream raw materials:

N⁴-benzoyl-2'-O-(tetrahydrofuran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

N⁴-benzoyl-2'-O-tetrahydropyranylcytidine

4-N-benzoyl-2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)cytidine

4-[(2R,3R,4R,5R)-2-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-4-methoxy-heptanedioic acid dimethyl ester