Toluene-4-sulfonic acid 2-((2S,3R)-3-[1,3]dioxolan-2-yl-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 2-((2S,3R)-3-[1,3]dioxolan-2-yl-5-oxo-tetrahydro-furan-2-yl)-ethyl ester
• CAS No.: 244612-56-4
• Molecular Formula: C₁₆H₂₀O₇S
• Molecular Weight: 356.397

Synonyms:Toluene-4-sulfonic acid 2-((2S,3R)-3-[1,3]dioxolan-2-yl-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

Chemical Property of Toluene-4-sulfonic acid 2-((2S,3R)-3-[1,3]dioxolan-2-yl-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

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Technology Process of Toluene-4-sulfonic acid 2-((2S,3R)-3-[1,3]dioxolan-2-yl-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

There total 10 articles about Toluene-4-sulfonic acid 2-((2S,3R)-3-[1,3]dioxolan-2-yl-5-oxo-tetrahydro-furan-2-yl)-ethyl 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: 90.0%

p-toluenesulfonyl chloride (98-59-9) + (4R,5S)-4-[1,3]Dioxolan-2-yl-5-(2-hydroxy-ethyl)-dihydro-furan-2-one (244612-55-3) → Toluene-4-sulfonic acid 2-((2S,3R)-3-[1,3]dioxolan-2-yl-5-oxo-tetrahydro-furan-2-yl)-ethyl ester (244612-56-4)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1016/S0040-4039(99)00855-2

Reference yield:

(2S,3E,5S)-1,2,5,6-tetrahydroxy-1,2:5,6-di-O-isopropylidene-hex-3-ene (3427-24-5) → Toluene-4-sulfonic acid 2-((2S,3R)-3-[1,3]dioxolan-2-yl-5-oxo-tetrahydro-furan-2-yl)-ethyl ester (244612-56-4)

Guidance literature:

Multi-step reaction with 10 steps

1: AcOH, H₂O / 1 h / 40 °C

2: imidazole / tetrahydrofuran; dimethylformamide / 2 h / 0 °C

3: 98 percent / mol. sieves 4 Angstroem / benzene / 2.5 h / Heating

4: Et₃N / tetrahydrofuran / 9 h / Ambient temperature

5: I₂, NaHCO₃ / tetrahydrofuran; H₂O / 7 h / -10 °C

6: 86 percent / TFA, MeOH / 6 h / Ambient temperature

7: NaIO₄ / tetrahydrofuran; H₂O / 0.33 h / Ambient temperature

8: TsOH / benzene / 16 h / Ambient temperature

9: 72 percent / Bu₃SnH, AIBN / toluene / 0.5 h / Heating

10: 90 percent / pyridine / 0 °C

With pyridine; 1H-imidazole; methanol; sodium periodate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; water; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(99)00855-2

Reference yield:

(2S,3E,5S)-1,2,5,6-tetrahydroxy-hex-3-ene (6027-47-0) → Toluene-4-sulfonic acid 2-((2S,3R)-3-[1,3]dioxolan-2-yl-5-oxo-tetrahydro-furan-2-yl)-ethyl ester (244612-56-4)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole / tetrahydrofuran; dimethylformamide / 2 h / 0 °C

2: 98 percent / mol. sieves 4 Angstroem / benzene / 2.5 h / Heating

3: Et₃N / tetrahydrofuran / 9 h / Ambient temperature

4: I₂, NaHCO₃ / tetrahydrofuran; H₂O / 7 h / -10 °C

5: 86 percent / TFA, MeOH / 6 h / Ambient temperature

6: NaIO₄ / tetrahydrofuran; H₂O / 0.33 h / Ambient temperature

7: TsOH / benzene / 16 h / Ambient temperature

8: 72 percent / Bu₃SnH, AIBN / toluene / 0.5 h / Heating

9: 90 percent / pyridine / 0 °C

With pyridine; 1H-imidazole; methanol; sodium periodate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(99)00855-2

upstream raw materials:

p-toluenesulfonyl chloride

(4R,5S)-4-[1,3]Dioxolan-2-yl-5-(2-hydroxy-ethyl)-dihydro-furan-2-one

(2S,3E,5S)-1,2,5,6-tetrahydroxy-1,2:5,6-di-O-isopropylidene-hex-3-ene

(2S,3E,5S)-1,2,5,6-tetrahydroxy-hex-3-ene

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