Toluene-4-sulfonic acid (4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl ester
• CAS No.: 100017-25-2
• Molecular Formula: C₁₅H₂₀O₅S
• Molecular Weight: 312.387

Synonyms:Toluene-4-sulfonic acid (4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl ester

There total 31 articles about Toluene-4-sulfonic acid (4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-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: 95.0%

(4S,5R)-2,2-dimethyl-4-hydroxymethyl-5-vinyl-1,3-dioxolane (114817-96-8,127758-25-2,99902-67-7) + p-toluenesulfonyl chloride (98-59-9) → (4S,5R)-2,2-dimethyl-4-(p-toluenesulfonyloxy)methyl-5-vinyl-1,3-dioxolane (100017-25-2,121469-42-9,121469-48-5,121469-49-6,133814-94-5,99902-68-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 48h; optical yield given as %de;

DOI:10.1039/c2ob25099c

Reference yield: 94.0%

(+/-)-2,3-Epoxy-1-tosyloxypent-4-ene (121405-00-3,121405-01-4) + acetone (67-64-1) → (+/-)-2,2-Dimethyl-4-tosyloxymethyl-5-vinyl-1,3-dioxolane (99902-68-8,100017-25-2,121469-42-9,121469-48-5,121469-49-6,133814-94-5)

Guidance literature:

With aluminium trichloride; for 24h; Ambient temperature;

DOI:10.1055/s-1988-27729

Reference yield: 80.0%

(-)-(2S,3S)-2,3-Epoxy-1-tosyloxypent-4-ene (121405-01-4) + acetone (67-64-1) → (4S,5R)-2,2-dimethyl-4-(p-toluenesulfonyloxy)methyl-5-vinyl-1,3-dioxolane (100017-25-2,121469-42-9,121469-48-5,121469-49-6,133814-94-5,99902-68-8)

Guidance literature:

With aluminium trichloride; for 24h; Ambient temperature;

DOI:10.1055/s-1988-27729

upstream raw materials:

(4S,5R)-2,2-dimethyl-4-hydroxymethyl-5-vinyl-1,3-dioxolane

p-toluenesulfonyl chloride

(2R)-1-O-p-tosyl-4-pentene-1,2,3-triol

2,2-dimethoxy-propane

Downstream raw materials:

(+)-(2S,3R)-1-Tosyloxypent-4-en-2,3-diol

(-)-(1S,5R,7R)-5-Methyl-3-phenylsulfonyl-7-vinyl-6,8-dioxabicyclo<3.2.1>octane

(-)-(2R,4S,5R)-2-Methyl-2-<2-(phenylsulfonyl)ethyl>-4-tosyloxymethyl-5-vinyl-1,3-dioxolane

(+/-)-2,2-Dimethyl-4-<2-phenylsulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl>-5-vinyl-1,3-dioxolane

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