N-Benzoyl-2'-O-[(methylthio)methyl]-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]cytidine

Base Information

• Chemical Name: N-Benzoyl-2'-O-[(methylthio)methyl]-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]cytidine
• CAS No.: 139434-68-7
• Molecular Formula: C30H47 N3 O7 S Si2
• Molecular Weight: 649.956
• Mol file: 139434-68-7.mol

Synonyms:6H-Furo[3,2-f]-1,3,5,2,4-trioxadisilocin,cytidine deriv.

Chemical Property of N-Benzoyl-2'-O-[(methylthio)methyl]-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]cytidine

Chemical Property:

• PSA: 135.44000
• Density: 1.21
• LogP: 6.12810

Purity/Quality:

97% ^*data from raw suppliers

N-Benzoyl-2'-O-[(methylthio)methyl]-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-cytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-Benzoyl-2'-O-[(methylthio)methyl]-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]cytidine

There total 5 articles about N-Benzoyl-2'-O-[(methylthio)methyl]-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-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: 80.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine (69304-43-4) → N-benzoyl-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2′-O-[(methylthio)methyl]cytidine (139434-68-7)

Guidance literature:

With acetic anhydride; acetic acid; at 20 ℃;

DOI:10.1016/j.bmc.2018.10.025

Reference yield:

3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N6-benzoyladenosine (79154-57-7) + dimethyl sulfoxide (67-68-5,8070-53-9) → N-benzoyl-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2′-O-[(methylthio)methyl]cytidine (139434-68-7)

Guidance literature:

3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N₆-benzoyladenosine; dimethyl sulfoxide; With acetic anhydride; acetic acid; at 20 ℃; for 24h;

With water; potassium carbonate;

DOI:10.1021/ja0636587

Reference yield:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) → N-benzoyl-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2′-O-[(methylthio)methyl]cytidine (139434-68-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 3 h / 25 °C

2: acetic acid; Ac₂O / 48 h / 25 °C

With pyridine; acetic anhydride; acetic acid;

DOI:10.1021/ol0629824

upstream raw materials:

dimethyl sulfoxide

1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N⁴-benzoylcytosine

3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N₆-benzoyladenosine

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

Downstream raw materials:

C₃₆H₅₀N₄O₁₀Si₂

2'-O-azidomethyl-N⁴-benzoyl-3',5'-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)cytidine

2'-O-azidomethyl-N⁴-benzoylcytidine

N⁴-benzoyl-2'-O-(tert-butyldithiomethyl)cytidine

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