Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylmethyl] ester

Base Information

• Chemical Name: Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylmethyl] ester
• CAS No.: 183374-94-9
• Molecular Formula: C₂₈H₃₄N₂O₆SSi
• Molecular Weight: 554.739
• Mol file: 183374-94-9.mol

Synonyms:Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylmethyl] ester

Chemical Property of Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylmethyl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylmethyl] ester

There total 3 articles about Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-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: 65.0%

1-[(2R,3R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-4-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (183374-93-8) + tiolacetic acid (507-09-5) → Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylmethyl] ester (183374-94-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/jo960669h

Reference yield:

1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil (183374-92-7) → Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylmethyl] ester (183374-94-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / aq. NaOH / methanol / 1 h / Ambient temperature

2: 65 percent / PPh₃, DIAD / acetonitrile; tetrahydrofuran / 2 h / Ambient temperature

With sodium hydroxide; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jo960669h

Reference yield:

2-benzoyl-3-[(benzoyloxy)methyl]-5-(tert-butyldiphenylsilyl)-3-deoxy-1-O-methyl-α- and β-ribofuranose → Thioacetic acid S-[(2S,3S,4R,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylmethyl] ester (183374-94-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) MSTFA, 2.) TMSTf / 1.) CH₃CN, 10 min, 2.) CH₃CN, 40 deg C, 12 h

2: 70 percent / aq. NaOH / methanol / 1 h / Ambient temperature

3: 65 percent / PPh₃, DIAD / acetonitrile; tetrahydrofuran / 2 h / Ambient temperature

With sodium hydroxide; di-isopropyl azodicarboxylate; TMSTf; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; triphenylphosphine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jo960669h

upstream raw materials:

1-[(2R,3R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-4-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

tiolacetic acid

1-{2'-benzoyl-3'-[(benzoyloxy)methyl]-5'-(tert-butyldiphenylsilyl)-3'-deoxy-β-ribofuranosyl}uracil

Downstream raw materials:

C₅₃H₆₄N₄O₁₁SSi₂

C₅₅H₆₆N₄O₁₂SSi₂

C₅₄H₆₄N₄O₁₀SSi₂

C₄₄H₄₈N₄O₁₄S