Benzoic acid (2S,3R,4R,5S)-4-acetoxy-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4R,5S)-4-acetoxy-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 187733-82-0
• Molecular Formula: C₄₈H₅₃N₃O₁₀SSi
• Molecular Weight: 892.114
• Mol file: 187733-82-0.mol

Synonyms:Benzoic acid (2S,3R,4R,5S)-4-acetoxy-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2S,3R,4R,5S)-4-acetoxy-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3R,4R,5S)-4-acetoxy-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester

There total 5 articles about Benzoic acid (2S,3R,4R,5S)-4-acetoxy-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-5-phenylsulfanyl-tetrahydro-furan-2-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: 82.0%

acetic anhydride (108-24-7) + Benzoic acid (2S,3S,4R,5S)-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-4-hydroxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester (171762-56-4) → Benzoic acid (2S,3R,4R,5S)-4-acetoxy-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester (187733-82-0)

Guidance literature:

With pyridine; for 20h; Ambient temperature;

Reference yield:

thiophenol (108-98-5) → Benzoic acid (2S,3R,4R,5S)-4-acetoxy-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester (187733-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / TFA / 7 h

2: 82 percent / pyridine / 20 h / Ambient temperature

With pyridine; trifluoroacetic acid;

Reference yield:

5'-Amino-3'-tert-butyldiphenylsilyl-5'-deoxythymidine (146557-63-3) → Benzoic acid (2S,3R,4R,5S)-4-acetoxy-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester (187733-82-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Et₃N, O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, HOBT, 2.) Et₃N / 1.) MeCN, THF, r.t., 1 h, 2.) r.t., 12 h

2: 51 percent / TFA / 7 h

3: 82 percent / pyridine / 20 h / Ambient temperature

With pyridine; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; trifluoroacetic acid;

upstream raw materials:

acetic anhydride

Benzoic acid (2S,3S,4R,5S)-3-({[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-4-hydroxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester

thiophenol

5'-Amino-3'-tert-butyldiphenylsilyl-5'-deoxythymidine

Downstream raw materials:

C₆₁H₆₇N₅O₁₃Si

C₅₉H₆₅N₅O₁₂Si

C₄₇H₅₃N₅O₁₂Si

2'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-3'-deoxy-3'-{[N-(5'-deoxythymidine-5'-yl)carboxamido]methyl}ribothymidine