N³-benzyloxymethyl-1-[2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-2-fluoromethyl-4-thio-β-D-arabinofuranosyl]thymine

Base Information

• Chemical Name: N³-benzyloxymethyl-1-[2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-2-fluoromethyl-4-thio-β-D-arabinofuranosyl]thymine
• CAS No.: 753007-88-4
• Molecular Formula: C₃₁H₅₁FN₂O₅SSi₂
• Molecular Weight: 638.992

Synonyms:N³-benzyloxymethyl-1-[2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-2-fluoromethyl-4-thio-β-D-arabinofuranosyl]thymine

Chemical Property of N³-benzyloxymethyl-1-[2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-2-fluoromethyl-4-thio-β-D-arabinofuranosyl]thymine

Chemical Property:

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Technology Process of N³-benzyloxymethyl-1-[2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-2-fluoromethyl-4-thio-β-D-arabinofuranosyl]thymine

There total 14 articles about N³-benzyloxymethyl-1-[2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-2-fluoromethyl-4-thio-β-D-arabinofuranosyl]thymine 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: 63.0%

N3-benzyloxymethyl-1-[3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-2-hydroxymethyl-4-thio-β-D-arabinofuranosyl]thymine (753007-87-3) → N3-benzyloxymethyl-1-[2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-2-fluoromethyl-4-thio-β-D-arabinofuranosyl]thymine (753007-88-4)

Guidance literature:

With sodium carbonate; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at 0 ℃;

DOI:10.1021/ol040035u

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → N3-benzyloxymethyl-1-[2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-2-fluoromethyl-4-thio-β-D-arabinofuranosyl]thymine (753007-88-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / DBN / dimethylformamide / 0 °C

2: 99 percent / NaOMe / methanol / 4 h / 0 °C

3: 63 percent / Na₂CO₃; DAST / CH₂Cl₂ / 0 °C

With 2,6-dichloro-benzonitrile; sodium methylate; sodium carbonate; 4,4'-diaminostilbene-2,2'-disulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol040035u

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → N3-benzyloxymethyl-1-[2-deoxy-3,5-bis-O-(t-butyldimethylsilyl)-2-fluoromethyl-4-thio-β-D-arabinofuranosyl]thymine (753007-88-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / acetonitrile; CH₂Cl₂ / 0 °C

2: 96 percent / Bu₃SnH; Et₃B; O₂ / toluene / 1 h / -70 °C

3: Bu₄NF*3H₂O / tetrahydrofuran / 1 h / 0 °C

4: 199.1 mg / dimethylformamide / 60 °C

5: 88 percent / DBN / dimethylformamide / 0 °C

6: 99 percent / NaOMe / methanol / 4 h / 0 °C

7: 63 percent / Na₂CO₃; DAST / CH₂Cl₂ / 0 °C

With triethyl borane; 2,6-dichloro-benzonitrile; tetrabutyl ammonium fluoride; oxygen; tri-n-butyl-tin hydride; sodium methylate; sodium carbonate; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ol040035u

upstream raw materials:

N³-benzyloxymethyl-1-[3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-2-hydroxymethyl-4-thio-β-D-arabinofuranosyl]thymine

Benzyloxymethyl chloride

thymin

1,4-anhydro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-4-thio-D-erythro-pent-1-enitol

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