(1R,4S,6S)-4-Hydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-1-(toluene-4-sulfonyl)-cyclohex-2-enecarboxylic acid methyl ester

Base Information

Chemical Name:(1R,4S,6S)-4-Hydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-1-(toluene-4-sulfonyl)-cyclohex-2-enecarboxylic acid methyl ester
CAS No.:104464-05-3
Molecular Formula:C₂₅H₃₀O₆S
Molecular Weight:458.576
Hs Code.:

Synonyms:(1R,4S,6S)-4-Hydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-1-(toluene-4-sulfonyl)-cyclohex-2-enecarboxylic acid methyl ester

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Chemical Property of (1R,4S,6S)-4-Hydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-1-(toluene-4-sulfonyl)-cyclohex-2-enecarboxylic acid methyl ester

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Technology Process of (1R,4S,6S)-4-Hydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-1-(toluene-4-sulfonyl)-cyclohex-2-enecarboxylic acid methyl ester

There total 1 articles about (1R,4S,6S)-4-Hydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-1-(toluene-4-sulfonyl)-cyclohex-2-enecarboxylic 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: 93.0%

: 124-41-4
sodium methylate

: 104464-04-2
(1S,4R,8S)-8-((S)-2-Methyl-1-phenyl-propoxy)-4-(toluene-4-sulfonyl)-2-oxa-bicyclo[2.2.2]oct-5-en-3-one

: 104464-05-3
(1R,4S,6S)-4-Hydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-1-(toluene-4-sulfonyl)-cyclohex-2-enecarboxylic acid methyl ester

Guidance literature:: In methanol; dichloromethane; at -78 ℃; for 0.0833333h;
DOI:10.1021/ja00283a036

Reference yield:

: 104464-05-3
(1R,4S,6S)-4-Hydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-1-(toluene-4-sulfonyl)-cyclohex-2-enecarboxylic acid methyl ester

: 104528-69-0
methyl 3,4,5-tri-O-acetyl-4-epi-shikimate

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) aluminum amalgam; 2.) p-nitroperbenzoic acid / 1.) reflux; 2.) 0 deg C, chloroform, room temperature, 16 h

2: DBU / CH₂Cl₂ / -78 deg C, 5 min, room temperature, 2.5 h

3: hydrogen / 10percent Pd-C / ethanol / 12 h

4: trifluoroacetic acid / CH₂Cl₂ / 0 °C

5: p-toluenesulfonic acid / CH₂Cl₂ / 20 h / Ambient temperature

6: 1.) triethylamine, methanesulfonyl chloride; 2.) DBU / 1.) dichloromethane, 0 deg C, 3 h; 2.) dichloromethane, 0 deg C

7: 1.) lithium diisopropylamide; 2.) acetic acid / 1.) dichloromethane, THF, -100 deg C, 70 min; 2.) THF, -70 deg C, 20 min, room temperature

8: m-CPBA / CH₂Cl₂ / 48 h / 0 °C

9: DBU / CH₂Cl₂ / 18 h / 0 °C

10: 1.) p-toluenesulfonic acid; 2.) 4-(dimethylamino)pyridine, triethylamine / 1.) methanol, room temperature, 9 h; 2.) 0 deg C, dichloromethane, room temperature, 2 h

With 4-nitroperbenzoic acid; dmap; aluminium amalgam; hydrogen; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In ethanol; dichloromethane;
DOI:10.1021/ja00283a036

Reference yield:

: 104464-05-3
(1R,4S,6S)-4-Hydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-1-(toluene-4-sulfonyl)-cyclohex-2-enecarboxylic acid methyl ester

: (2S,4S,5R)-2,4,5-Trihydroxy-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) aluminum amalgam; 2.) p-nitroperbenzoic acid / 1.) reflux; 2.) 0 deg C, chloroform, room temperature, 16 h

2: DBU / CH₂Cl₂ / -78 deg C, 5 min, room temperature, 2.5 h

3: hydrogen / 10percent Pd-C / ethanol / 12 h

4: trifluoroacetic acid / CH₂Cl₂ / 0 °C

With 4-nitroperbenzoic acid; aluminium amalgam; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane;
DOI:10.1021/ja00283a036