Toluene-4-sulfonic acid (1S,3S,5R)-1-(6-oxa-bicyclo[3.1.0]hex-3-yl)methyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (1S,3S,5R)-1-(6-oxa-bicyclo[3.1.0]hex-3-yl)methyl ester
CAS No.:852364-14-8
Molecular Formula:C₁₃H₁₆O₄S
Molecular Weight:268.334
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (1S,3S,5R)-1-(6-oxa-bicyclo[3.1.0]hex-3-yl)methyl ester

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Chemical Property of Toluene-4-sulfonic acid (1S,3S,5R)-1-(6-oxa-bicyclo[3.1.0]hex-3-yl)methyl ester

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Technology Process of Toluene-4-sulfonic acid (1S,3S,5R)-1-(6-oxa-bicyclo[3.1.0]hex-3-yl)methyl ester

There total 9 articles about Toluene-4-sulfonic acid (1S,3S,5R)-1-(6-oxa-bicyclo[3.1.0]hex-3-yl)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: 93.0%

: 72656-82-7
anti-3-(Hydroxymethyl)-6-oxabicyclo<3.1.0>hexane

: 98-59-9
p-toluenesulfonyl chloride

: 852364-14-8
Toluene-4-sulfonic acid (1S,3S,5R)-1-(6-oxa-bicyclo[3.1.0]hex-3-yl)methyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 16h;
DOI:10.1055/s-2005-863745

Reference yield:

: 58101-60-3
methyl cyclopent-3-ene-1-carboxylate

: 852364-14-8
Toluene-4-sulfonic acid (1S,3S,5R)-1-(6-oxa-bicyclo[3.1.0]hex-3-yl)methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 - 20 °C

2: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C

3: 97 percent / MCPBA / CH₂Cl₂ / 1 h / 0 - 20 °C

4: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

5: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 0 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2005-863745

Reference yield:

: 25125-21-7
4-(hydroxymethyl)cyclopentene

: 852364-14-8
Toluene-4-sulfonic acid (1S,3S,5R)-1-(6-oxa-bicyclo[3.1.0]hex-3-yl)methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C

2: 97 percent / MCPBA / CH₂Cl₂ / 1 h / 0 - 20 °C

3: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

4: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 0 °C

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2005-863745