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

Base Information

• Chemical Name: N³-benzyloxymethyl-1-[3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-2-hydroxymethyl-4-thio-β-D-arabinofuranosyl]thymine
• CAS No.: 753007-87-3
• Molecular Formula: C₃₁H₅₂N₂O₆SSi₂
• Molecular Weight: 637.001

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 13 articles about N³-benzyloxymethyl-1-[3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-2-hydroxymethyl-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: 99.0%

1-[2-acetyloxymethyl-3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-4-thio-β-D-arabinofuranosyl]-N3-benzyloxymethylthymine (753007-86-2) → N3-benzyloxymethyl-1-[3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-2-hydroxymethyl-4-thio-β-D-arabinofuranosyl]thymine (753007-87-3)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 4h;

DOI:10.1021/ol040035u

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → N3-benzyloxymethyl-1-[3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-2-hydroxymethyl-4-thio-β-D-arabinofuranosyl]thymine (753007-87-3)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 2,6-dichloro-benzonitrile; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol040035u

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → N3-benzyloxymethyl-1-[3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-2-hydroxymethyl-4-thio-β-D-arabinofuranosyl]thymine (753007-87-3)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/ol040035u

upstream raw materials:

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

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

Downstream raw materials:

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

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