Toluene-4-sulfonic acid (S)-1-[5,5-dimethyl-2-((E)-styryl)-[1,3]dioxan-2-yl]-ethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (S)-1-[5,5-dimethyl-2-((E)-styryl)-[1,3]dioxan-2-yl]-ethyl ester
• CAS No.: 103635-81-0
• Molecular Formula: C₂₃H₂₈O₅S
• Molecular Weight: 416.538

Synonyms:Toluene-4-sulfonic acid (S)-1-[5,5-dimethyl-2-((E)-styryl)-[1,3]dioxan-2-yl]-ethyl ester

Chemical Property of Toluene-4-sulfonic acid (S)-1-[5,5-dimethyl-2-((E)-styryl)-[1,3]dioxan-2-yl]-ethyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (S)-1-[5,5-dimethyl-2-((E)-styryl)-[1,3]dioxan-2-yl]-ethyl ester

There total 3 articles about Toluene-4-sulfonic acid (S)-1-[5,5-dimethyl-2-((E)-styryl)-[1,3]dioxan-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: 96.0%

2, 2, 5, 5, 8, 8-hexamethyl-3, 7-dioxa-2, 8-disilanonane (2117-23-9) + Methanesulfonic acid (E)-(S)-1-methyl-2-oxo-4-phenyl-but-3-enyl ester → Toluene-4-sulfonic acid (S)-1-[5,5-dimethyl-2-((E)-styryl)-[1,3]dioxan-2-yl]-ethyl ester (103635-81-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1246/cl.1986.13

Reference yield:

β-styrylmagnesium bromide (30094-01-0,35672-47-0,56516-81-5) → Toluene-4-sulfonic acid (S)-1-[5,5-dimethyl-2-((E)-styryl)-[1,3]dioxan-2-yl]-ethyl ester (103635-81-0)

Guidance literature:

Multi-step reaction with 3 steps

2: 79 percent / pyridine / 1.5 h / 0 °C

3: 96 percent / trimethylsilyl trifluoromethansulfonate / CH₂Cl₂ / 20 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; In pyridine; dichloromethane;

DOI:10.1246/cl.1986.13

Reference yield:

(E)-(S)-4-Hydroxy-1-phenyl-pent-1-en-3-one (103635-88-7) → Toluene-4-sulfonic acid (S)-1-[5,5-dimethyl-2-((E)-styryl)-[1,3]dioxan-2-yl]-ethyl ester (103635-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / pyridine / 1.5 h / 0 °C

2: 96 percent / trimethylsilyl trifluoromethansulfonate / CH₂Cl₂ / 20 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; In pyridine; dichloromethane;

DOI:10.1246/cl.1986.13

upstream raw materials:

2, 2, 5, 5, 8, 8-hexamethyl-3, 7-dioxa-2, 8-disilanonane

β-styrylmagnesium bromide

(E)-(S)-4-Hydroxy-1-phenyl-pent-1-en-3-one

Downstream raw materials:

(E)-(S)-2-Methyl-4-phenyl-but-3-enoic acid 3-hydroxy-2,2-dimethyl-propyl ester

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