3'-(S)-(allenic sulfonyl)-5'-benzoyl-3'-deoxythymidine

Base Information

• Chemical Name: 3'-(S)-(allenic sulfonyl)-5'-benzoyl-3'-deoxythymidine
• CAS No.: 805236-64-0
• Molecular Formula: C₂₀H₂₀N₂O₇S
• Molecular Weight: 432.454
• Mol file: 805236-64-0.mol

Synonyms:3'-(S)-(allenic sulfonyl)-5'-benzoyl-3'-deoxythymidine

Chemical Property of 3'-(S)-(allenic sulfonyl)-5'-benzoyl-3'-deoxythymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-(S)-(allenic sulfonyl)-5'-benzoyl-3'-deoxythymidine

There total 6 articles about 3'-(S)-(allenic sulfonyl)-5'-benzoyl-3'-deoxythymidine 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: 83.0%

Benzoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-prop-2-ynylsulfanyl-tetrahydro-furan-2-ylmethyl ester (805236-62-8) → 3'-(S)-(allenic sulfonyl)-5'-benzoyl-3'-deoxythymidine (805236-64-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1055/s-2004-832807

Reference yield:

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine (104218-44-2) → 3'-(S)-(allenic sulfonyl)-5'-benzoyl-3'-deoxythymidine (805236-64-0)

Guidance literature:

Multi-step reaction with 6 steps

1: dimethylformamide / 90 °C

2: aq. KOH / ethanol / 3 h / 5 - 10 °C

3: DBU / CH₂Cl₂ / 15 h / 20 °C

4: 81 percent / aq. HOAc / 1.5 h / 90 °C

5: 88 percent / pyridine / 3 h / 0 - 20 °C

6: 83 percent / m-CPBA / CH₂Cl₂ / 1 h / 20 °C

With pyridine; potassium hydroxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-832807

Reference yield:

5'-O-trityl-3'-(acetylthio)-2',3'-dideoxythymidine (805236-59-3) → 3'-(S)-(allenic sulfonyl)-5'-benzoyl-3'-deoxythymidine (805236-64-0)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. KOH / ethanol / 3 h / 5 - 10 °C

2: DBU / CH₂Cl₂ / 15 h / 20 °C

3: 81 percent / aq. HOAc / 1.5 h / 90 °C

4: 88 percent / pyridine / 3 h / 0 - 20 °C

5: 83 percent / m-CPBA / CH₂Cl₂ / 1 h / 20 °C

With pyridine; potassium hydroxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane;

DOI:10.1055/s-2004-832807

upstream raw materials:

Benzoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-prop-2-ynylsulfanyl-tetrahydro-furan-2-ylmethyl ester

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine

5'-O-trityl-3'-(acetylthio)-2',3'-dideoxythymidine

3'-deoxy-3'-(S)-(propargylthio)thymidine

Downstream raw materials:

Benzoic acid (2R,3S,5R)-3-{2-[9-((2R,4S,5R)-4-acetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-prop-2-ene-1-sulfonyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Benzoic acid (2R,3S,5R)-3-{2-[9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-prop-2-ene-1-sulfonyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester