phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside

Base Information

• Chemical Name: phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside
• CAS No.: 1621691-61-9
• Molecular Formula: C₂₉H₃₇F₃O₆SSi
• Molecular Weight: 598.756

Synonyms:phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside

Chemical Property of phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside

Chemical Property:

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Technology Process of phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside

There total 5 articles about phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside 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%

phenyl 5-O-benzoyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside (1621691-60-8) + trifluoroacetic anhydride (407-25-0) → phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside (1621691-61-9)

Guidance literature:

With sodium 2,2,2-trifluoroacetate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.carres.2014.05.017

Reference yield:

phenyl 3,5-di-O-benzoyl-1-thio-α-D-arabinofuranoside (1379681-43-2) → phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside (1621691-61-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,4,6-trimethyl-pyridine / N,N-dimethyl-formamide / 1 h / 90 °C

2.1: sodium methylate / methanol / 48 h / 20 °C

2.2: Dowex 50Wx₄ (H⁺) ion-exchange resin

3.1: pyridine / dichloromethane / 1 h / 0 °C

4.1: sodium 2,2,2-trifluoroacetate / dichloromethane / 1 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; sodium methylate; sodium 2,2,2-trifluoroacetate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2014.05.017

Reference yield:

phenyl 2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside (1621691-57-3) → phenyl 5-O-benzoyl-3-O-trifluoroacetyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside (1621691-61-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 1 h / 0 °C

2: sodium 2,2,2-trifluoroacetate / dichloromethane / 1 h / 0 °C

With pyridine; sodium 2,2,2-trifluoroacetate; In dichloromethane;

DOI:10.1016/j.carres.2014.05.017

upstream raw materials:

phenyl 3,5-di-O-benzoyl-1-thio-α-D-arabinofuranoside

phenyl 2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside

phenyl 5-O-benzoyl-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside

trifluoroacetic anhydride

Downstream raw materials:

4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-α-D-arabinofuranosyl]-α-D-arabinofuranoside

4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[5-O-benzoyl-2-O-triisopropylsilyl-β-D-arabinofuranosyl]-α-D-arabinofuranoside

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