(1S,3R,4R)-3-Allyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(1S,3R,4R)-3-Allyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester
CAS No.:102437-37-6
Molecular Formula:C₁₉H₂₆O₅S
Molecular Weight:366.478
Hs Code.:

Synonyms:(1S,3R,4R)-3-Allyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

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Chemical Property of (1S,3R,4R)-3-Allyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

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Technology Process of (1S,3R,4R)-3-Allyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

There total 9 articles about (1S,3R,4R)-3-Allyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl 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: 92.4%

: 102437-36-5
(1S,3R,4R)-3-Allyl-4-hydroxymethyl-cyclohexanecarboxylic acid methyl ester

: 98-59-9
p-toluenesulfonyl chloride

: 102437-37-6
(1S,3R,4R)-3-Allyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

Guidance literature:: With pyridine; at 25 ℃; for 120h;
DOI:10.1021/jo00362a012

Reference yield:

: 3685-22-1,3685-26-5,17419-81-7
4-hydroxycyclohexanecarboxylic acid

: 102437-37-6
(1S,3R,4R)-3-Allyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 91.1 percent / diethyl ether / 25 °C

2: Celite, pyridinium chlorochromate (PCC) / CH₂Cl₂ / 3 h / 25 °C

3: p-toluenesulfonic aicd monohydrate, 2,2-dimethoxypropane / benzene / Heating

4: 60 percent / tetrahydrofuran; toluene / 1.) 0 deg C 1 h, 2.) 25 deg C, 3 h

5: 87.3 percent / 2N aq. HCl / tetrahydrofuran / 24 h / 25 °C

6: NaOMe / methanol / 48 h / Heating

7: 96 percent / NaBH₄ / methanol / 0.25 h / 0 °C

8: 92.4 percent / pyridine / 120 h / 25 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; Celite; sodium methylate; toluene-4-sulfonic acid; 2,2-dimethoxy-propane; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; benzene;
DOI:10.1021/jo00362a012

Reference yield:

: 99-96-7
4-hydroxy-benzoic acid

: 102437-37-6
(1S,3R,4R)-3-Allyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 97 percent / H₂ / 5percent Rh/Al₂O₃ / methanol / 24 h / 25 °C / 2585.7 Torr

2: 91.1 percent / diethyl ether / 25 °C

3: Celite, pyridinium chlorochromate (PCC) / CH₂Cl₂ / 3 h / 25 °C

4: p-toluenesulfonic aicd monohydrate, 2,2-dimethoxypropane / benzene / Heating

5: 60 percent / tetrahydrofuran; toluene / 1.) 0 deg C 1 h, 2.) 25 deg C, 3 h

6: 87.3 percent / 2N aq. HCl / tetrahydrofuran / 24 h / 25 °C

7: NaOMe / methanol / 48 h / Heating

8: 96 percent / NaBH₄ / methanol / 0.25 h / 0 °C

9: 92.4 percent / pyridine / 120 h / 25 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; Celite; hydrogen; sodium methylate; toluene-4-sulfonic acid; 2,2-dimethoxy-propane; pyridinium chlorochromate; Rh/Al₂O₃; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; benzene;
DOI:10.1021/jo00362a012