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

Base Information

• Chemical Name: Toluene-4-sulfonic acid (4S,5S)-2,2-dimethyl-5-trifluoromethanesulfonyloxymethyl-[1,3]dioxolan-4-ylmethyl ester
• CAS No.: 128162-83-4
• Molecular Formula: C₁₅H₁₉F₃O₈S₂
• Molecular Weight: 448.438

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

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

Chemical Property:

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

There total 1 articles about Toluene-4-sulfonic acid (4S,5S)-2,2-dimethyl-5-trifluoromethanesulfonyloxymethyl-[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:

trifluoromethylsulfonic anhydride (358-23-6) + (4S,5S)-4-hydroxymethyl-2,2-dimethyl-5-tosyloxymethyl-1,3-dioxolane (70831-49-1,73711-65-6,58789-44-9) → Toluene-4-sulfonic acid (4S,5S)-2,2-dimethyl-5-trifluoromethanesulfonyloxymethyl-[1,3]dioxolan-4-ylmethyl ester (128162-83-4)

Guidance literature:

With triethylamine; In dichloromethane; at -15 ℃; for 0.333333h;

DOI:10.1021/jo00301a038 DOI:10.1246/bcsj.64.721

Reference yield: 80.0%

nonylmagnesium bromide (39691-62-8) + Toluene-4-sulfonic acid (4S,5S)-2,2-dimethyl-5-trifluoromethanesulfonyloxymethyl-[1,3]dioxolan-4-ylmethyl ester (128162-83-4) → ((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl-4-methylbenzenesulfonate (122881-05-4)

Guidance literature:

With copper(I) bromide; In tetrahydrofuran; at 0 ℃; for 1.5h; chemoselective reaction;

DOI:10.1016/j.tet.2011.06.023

Reference yield:

Toluene-4-sulfonic acid (4S,5S)-2,2-dimethyl-5-trifluoromethanesulfonyloxymethyl-[1,3]dioxolan-4-ylmethyl ester (128162-83-4) + (4-(benzyloxy)phenyl)magnesium bromide (120186-59-6) → (2S,3S)-4-(4'-benzyloxyphenyl)-2,3-O-isopropylidenedioxy-1-p-toluenesulfonyloxybutane (177959-34-1)

Guidance literature:

With copper(I) bromide; In diethyl ether; at 0 ℃; Yield given;

DOI:10.1016/0040-4039(96)00670-3

upstream raw materials:

trifluoromethylsulfonic anhydride

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

Downstream raw materials:

Toluene-4-sulfonic acid (4S,5S)-5-[4-(tert-butyl-dimethyl-silanyloxy)-but-2-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

(4S,5S)-4-Benzyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane

(2S,3S)-4-(4'-benzyloxyphenyl)-2,3-O-isopropylidenedioxy-1-p-toluenesulfonyloxybutane

Toluene-4-sulfonic acid (2S,3S)-4-(4-benzyloxy-phenyl)-2,3-dihydroxy-butyl ester

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