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

Base Information

• Chemical Name: 1-[2-acetyloxymethyl-3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-4-thio-β-D-arabinofuranosyl]-N³-benzyloxymethylthymine
• CAS No.: 753007-86-2
• Molecular Formula: C₃₃H₅₄N₂O₇SSi₂
• Molecular Weight: 679.038

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 1-[2-acetyloxymethyl-3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-4-thio-β-D-arabinofuranosyl]-N³-benzyloxymethylthymine 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: 88.0%

Benzyloxymethyl chloride (3587-60-8) + 1-[2-acetyloxymethyl-3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-4-thio-β-D-arabinofuranosyl]thymine (753007-79-3) → 1-[2-acetyloxymethyl-3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-4-thio-β-D-arabinofuranosyl]-N3-benzyloxymethylthymine (753007-86-2)

Guidance literature:

With 2,6-dichloro-benzonitrile; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1021/ol040035u

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → 1-[2-acetyloxymethyl-3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-4-thio-β-D-arabinofuranosyl]-N3-benzyloxymethylthymine (753007-86-2)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/ol040035u

Reference yield:

1,4-anhydro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-4-thio-D-erythro-pent-1-enitol (209048-61-3) → 1-[2-acetyloxymethyl-3,5-bis-O-(t-butyldimethylsilyl)-2-deoxy-4-thio-β-D-arabinofuranosyl]-N3-benzyloxymethylthymine (753007-86-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: LDA / tetrahydrofuran / 0.5 h / -70 °C

1.2: 86 percent / PhSO₂Cl / tetrahydrofuran / 0.5 h / -70 °C

2.1: LTMP / tetrahydrofuran / 0.5 h / -70 °C

2.2: tetrahydrofuran / 0.5 h / -70 °C

2.3: 85 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / 0 °C

3.1: liquid NH₃; Na / diethyl ether / 0.5 h / -80 °C

4.1: 580.2 mg / i-Pr₂NEt; DMAP / CH₂Cl₂

5.1: 92 percent / acetonitrile; CH₂Cl₂ / 0 °C

6.1: 96 percent / Bu₃SnH; Et₃B; O₂ / toluene / 1 h / -70 °C

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

8.1: 199.1 mg / dimethylformamide / 60 °C

9.1: 88 percent / DBN / dimethylformamide / 0 °C

With dmap; triethyl borane; 2,6-dichloro-benzonitrile; 2,2,6,6-tetramethylpiperidinyl-lithium; tetrabutyl ammonium fluoride; ammonia; oxygen; tri-n-butyl-tin hydride; sodium; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ol040035u

upstream raw materials:

Benzyloxymethyl chloride

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

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

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

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