(1R,2S,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid

Base Information

• Chemical Name: (1R,2S,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid
• CAS No.: 123538-57-8
• Molecular Formula: C₁₈H₂₂O₆S
• Molecular Weight: 366.435

Synonyms:(1R,2S,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid

Chemical Property of (1R,2S,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2S,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid

There total 2 articles about (1R,2S,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid 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: 64.0%

methyl 1-(trimethylsilyl)-2-<(trimethylsilyl)methyl>prop-1-en-3-yl carbonate (103693-94-3,112373-93-0) + (E)-(4'S)-2-(2',2'-dimethyl-1',3'-dioxalan-4'-yl)vinyl phenyl sulphone (100289-50-7) → (1R,2S,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid (123538-57-8)

Guidance literature:

palladium diacetate; triisopropyl phosphite; In toluene; at 80 ℃; for 6h; Yields of byproduct given;

DOI:10.1021/ja00201a032

Reference yield:

methyl 1-(trimethylsilyl)-2-<(trimethylsilyl)methyl>prop-1-en-3-yl carbonate (103693-94-3,112373-93-0) + 3(S),4-Dihydroxy-1-(phenylsulfonyl)-(E)-1-butene acetonide (123538-50-1) → (1R,2S,3R)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid (123488-12-0) + (1S,2R,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid (123488-12-0,123538-56-7,123538-57-8)

Guidance literature:

palladium diacetate; triisopropyl phosphite; In 1,4-dioxane; at 80 ℃; for 5h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00201a032

Reference yield: 73.0%

(1R,2S,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid (123538-57-8) + triethyl phosphite (122-52-1) → (1R,2S,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid ethyl ester (123488-13-1)

Guidance literature:

With diethylazodicarboxylate; In 1,2-dimethoxyethane; for 12h; Ambient temperature;

DOI:10.1021/ja00201a032

upstream raw materials:

methyl 1-(trimethylsilyl)-2-<(trimethylsilyl)methyl>prop-1-en-3-yl carbonate

(E)-(4'S)-2-(2',2'-dimethyl-1',3'-dioxalan-4'-yl)vinyl phenyl sulphone

3(S),4-Dihydroxy-1-(phenylsulfonyl)-(E)-1-butene acetonide

Downstream raw materials:

(1R,2S,3S)-3-Benzenesulfonyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methylene-cyclopentanecarboxylic acid ethyl ester

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