Toluene-4-sulfonic acid (R)-2-cyclopentyl-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-allyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (R)-2-cyclopentyl-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-allyl ester
CAS No.:132101-48-5
Molecular Formula:C₂₀H₂₈O₅S
Molecular Weight:380.505
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (R)-2-cyclopentyl-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-allyl ester

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Chemical Property of Toluene-4-sulfonic acid (R)-2-cyclopentyl-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-allyl ester

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Technology Process of Toluene-4-sulfonic acid (R)-2-cyclopentyl-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-allyl ester

There total 11 articles about Toluene-4-sulfonic acid (R)-2-cyclopentyl-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-allyl 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: 82.0%

: 13438-45-4
zinc(II) tosylate

: 132101-42-9
erythro-6-cyclopentyl-2,5-dihydroxy-3,4-epoxy-2-methyl-6-heptene

: 132101-48-5
Toluene-4-sulfonic acid (R)-2-cyclopentyl-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-allyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In benzene; for 2h; Ambient temperature;
DOI:10.1021/ja00008a044

Reference yield:

: 132101-64-5,27943-46-0
3-methyl-3-(tetrahydro-2H-pyran-2-yloxy)butyne

: 132101-48-5
Toluene-4-sulfonic acid (R)-2-cyclopentyl-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-allyl ester

Guidance literature:: Multi-step reaction with 5 steps

2: 90 percent / pyridinium p-toluenesulfonate / ethanol / 0.33 h / 55 °C

3: 94 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

4: 1.) t-BuOOH, VO(acac)2, 2.) Bu₄N⁽¹⁺⁾F^(1-) / 1.) benzene, 40 deg C, 30 min, 2.) THF, RT, overnight

5: 82 percent / Ph₃P, diethyl azodicarboxylate (DEAD) / benzene / 2 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In ethanol; dichloromethane; benzene;
DOI:10.1021/ja00008a044

Reference yield:

: 18928-91-1
diethyl 2-cyclopentylmalonate

: 132101-48-5
Toluene-4-sulfonic acid (R)-2-cyclopentyl-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-allyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 89 percent / KOH / ethanol; H₂O / 12 h / 0 - 20 °C

2: 53 percent / CH₃COOH, CH₃COONa, 30percent aq. CH₂O, Et₂NH / Heating

3: 88 percent / i-Bu₂AlH / diethyl ether / 5 h / -78 - 20 °C

4: 80 percent / MnO₂ / CH₂Cl₂ / 96 h

6: 90 percent / pyridinium p-toluenesulfonate / ethanol / 0.33 h / 55 °C

7: 94 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

8: 1.) t-BuOOH, VO(acac)2, 2.) Bu₄N⁽¹⁺⁾F^(1-) / 1.) benzene, 40 deg C, 30 min, 2.) THF, RT, overnight

9: 82 percent / Ph₃P, diethyl azodicarboxylate (DEAD) / benzene / 2 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; manganese(IV) oxide; potassium hydroxide; formaldehyd; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; sodium acetate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetic acid; diethylamine; triethylamine; triphenylphosphine; diethylazodicarboxylate; In diethyl ether; ethanol; dichloromethane; water; benzene;
DOI:10.1021/ja00008a044