thioacetic acid S-(5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{2-[5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-trityloxy-ethyl)-tetrahydro-furan-3-ylmethanesulfonyl]-ethyl}-tetrahydro-furan-3-ylmethyl) ester

Base Information

• Chemical Name: thioacetic acid S-(5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{2-[5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-trityloxy-ethyl)-tetrahydro-furan-3-ylmethanesulfonyl]-ethyl}-tetrahydro-furan-3-ylmethyl) ester
• CAS No.: 664329-86-6
• Molecular Formula: C₄₅H₅₀N₄O₁₀S₂
• Molecular Weight: 871.045

Synonyms:thioacetic acid S-(5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{2-[5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-trityloxy-ethyl)-tetrahydro-furan-3-ylmethanesulfonyl]-ethyl}-tetrahydro-furan-3-ylmethyl) ester

Chemical Property of thioacetic acid S-(5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{2-[5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-trityloxy-ethyl)-tetrahydro-furan-3-ylmethanesulfonyl]-ethyl}-tetrahydro-furan-3-ylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of thioacetic acid S-(5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{2-[5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-trityloxy-ethyl)-tetrahydro-furan-3-ylmethanesulfonyl]-ethyl}-tetrahydro-furan-3-ylmethyl) ester

There total 8 articles about thioacetic acid S-(5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{2-[5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-trityloxy-ethyl)-tetrahydro-furan-3-ylmethanesulfonyl]-ethyl}-tetrahydro-furan-3-ylmethyl) ester 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: 91.0%

tiolacetic acid (507-09-5) + C43H48N4O10S (664329-44-6) → thioacetic acid S-(5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{2-[5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-trityloxy-ethyl)-tetrahydro-furan-3-ylmethanesulfonyl]-ethyl}-tetrahydro-furan-3-ylmethyl) ester (664329-86-6)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/hlca.200390244

Reference yield:

1-[3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5'-trideoxy-β-D-erythro-hexofuranosyl]thymine (651020-33-6) → thioacetic acid S-(5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{2-[5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-trityloxy-ethyl)-tetrahydro-furan-3-ylmethanesulfonyl]-ethyl}-tetrahydro-furan-3-ylmethyl) ester (664329-86-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / pyridine / CH₂Cl₂ / 3 h / 20 °C

2: 82 percent / Cs₂CO₃ / dimethylformamide / 4 h / 45 °C

3: oxone; NaOAc / methanol; tetrahydrofuran; H₂O

4: 350 mg / oxone; NaOAc / methanol; tetrahydrofuran; H₂O / 2 h

5: 93 percent / Bu₄NF / tetrahydrofuran / 2 h / 20 °C

6: 91 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 2 h / 20 °C

With pyridine; Oxone; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium acetate; caesium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 6: Mitsunobu reaction;

DOI:10.1002/hlca.200390244

Reference yield:

1-[6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]thymine (651020-38-1) → thioacetic acid S-(5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-{2-[5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-trityloxy-ethyl)-tetrahydro-furan-3-ylmethanesulfonyl]-ethyl}-tetrahydro-furan-3-ylmethyl) ester (664329-86-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / Cs₂CO₃ / tetrahydrofuran / 4 h / 45 °C

2: oxone; NaOAc / methanol; tetrahydrofuran; H₂O

3: 350 mg / oxone; NaOAc / methanol; tetrahydrofuran; H₂O / 2 h

4: 93 percent / Bu₄NF / tetrahydrofuran / 2 h / 20 °C

5: 91 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 2 h / 20 °C

With Oxone; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium acetate; caesium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; water; 5: Mitsunobu reaction;

DOI:10.1002/hlca.200390244

upstream raw materials:

tiolacetic acid

C₄₃H₄₈N₄O₁₀S

1-[6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]thymine

1-[2',3,'5'-trideoxy-3'-(mercaptomethyl)-6'-O-(triphenylmethyl)-β-D-erythro-hexofuranosyl]thymine

Downstream raw materials:

C₄₃H₄₈N₄O₉S₂

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