Benzoic acid (1R,2S,3R,5S)-3-acetylsulfanyl-5-hydroxy-2-((Z)-6-methoxycarbonyl-hex-2-enyl)-cyclohexylmethyl ester

Base Information

Chemical Name:Benzoic acid (1R,2S,3R,5S)-3-acetylsulfanyl-5-hydroxy-2-((Z)-6-methoxycarbonyl-hex-2-enyl)-cyclohexylmethyl ester
CAS No.:89560-19-0
Molecular Formula:C₂₄H₃₂O₆S
Molecular Weight:448.58
Hs Code.:

Synonyms:Benzoic acid (1R,2S,3R,5S)-3-acetylsulfanyl-5-hydroxy-2-((Z)-6-methoxycarbonyl-hex-2-enyl)-cyclohexylmethyl ester

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Chemical Property of Benzoic acid (1R,2S,3R,5S)-3-acetylsulfanyl-5-hydroxy-2-((Z)-6-methoxycarbonyl-hex-2-enyl)-cyclohexylmethyl ester

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Technology Process of Benzoic acid (1R,2S,3R,5S)-3-acetylsulfanyl-5-hydroxy-2-((Z)-6-methoxycarbonyl-hex-2-enyl)-cyclohexylmethyl ester

There total 18 articles about Benzoic acid (1R,2S,3R,5S)-3-acetylsulfanyl-5-hydroxy-2-((Z)-6-methoxycarbonyl-hex-2-enyl)-cyclohexylmethyl 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: 70.0%

: 78647-17-3,80408-49-7
methyl (1R*,2S*,4R*,6S*)-(Z)-2-acetylthio-4-hydroxy-6-hydroxymethylcyclohexanehept-5-enoate

: 98-88-4
benzoyl chloride

: 89560-19-0
Benzoic acid (1R,2S,3R,5S)-3-acetylsulfanyl-5-hydroxy-2-((Z)-6-methoxycarbonyl-hex-2-enyl)-cyclohexylmethyl ester

Guidance literature:: In pyridine; dichloromethane; 1.) -25 deg C, 2 h, 2.) r.t., 1 h;
DOI:10.1016/S0040-4020(01)88649-X

Reference yield:

: 17814-85-6
(4-carboxybutyl)triphenylphosphonium bromide

: 89560-19-0
Benzoic acid (1R,2S,3R,5S)-3-acetylsulfanyl-5-hydroxy-2-((Z)-6-methoxycarbonyl-hex-2-enyl)-cyclohexylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) DIBAL, 2.) dimsylsodium / 1.) toluene, -78 deg C, 20 min, 2.) DMSO, 45 deg C, 2 h, 3.) ether

2: 88 percent / PCC / CH₂Cl₂ / 1.5 h

3: 1.) NaBH₄, 2.) Et₃N / 1.) MeOH, -40 deg C, 15 min, 2.) CH₂Cl₂, -25 deg C, 30 min

4: 400 mg / NaH / dimethylsulfoxide / 24 h / 45 °C

5: PPTS / methanol / 1 h / 60 °C

6: 70 percent / pyridine; CH₂Cl₂ / 1.) -25 deg C, 2 h, 2.) r.t., 1 h

With sodium tetrahydroborate; dimsylsodium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; pyridinium chlorochromate; In pyridine; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/S0040-4020(01)88649-X

Reference yield:

: 2744-06-1,2825-02-7,89560-13-4,90972-15-9
trans-6-cyanomethyl-3-cyclohexenecarboxylic acid

: 89560-19-0
Benzoic acid (1R,2S,3R,5S)-3-acetylsulfanyl-5-hydroxy-2-((Z)-6-methoxycarbonyl-hex-2-enyl)-cyclohexylmethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 73 percent / KHCO₃, I₂, KI / H₂O / 6 h / Ambient temperature

2: 83 percent / DBU / benzene / 1.5 h / Ambient temperature

3: 100 percent / NaBH₄ / ethanol / 0.83 h / Ambient temperature

4: p-TsOH / CH₂Cl₂ / 0.33 h / 0 °C

5: 100 percent / 10percent NaOH / ethanol / 16 h / 100 °C

6: 1.) KI, I₂, KHCO₃, 2.) p-TsOH / 1.) water, 1 h, r.t., 2.) CH₂Cl₂

7: 92 percent / n-Bu₃SnH, ABIN / benzene / 0.5 h / 15 °C / Irradiation

8: 1.) DIBAL, 2.) dimsylsodium / 1.) toluene, -78 deg C, 20 min, 2.) DMSO, 45 deg C, 2 h, 3.) ether

9: 88 percent / PCC / CH₂Cl₂ / 1.5 h

10: 1.) NaBH₄, 2.) Et₃N / 1.) MeOH, -40 deg C, 15 min, 2.) CH₂Cl₂, -25 deg C, 30 min

11: 400 mg / NaH / dimethylsulfoxide / 24 h / 45 °C

12: PPTS / methanol / 1 h / 60 °C

13: 70 percent / pyridine; CH₂Cl₂ / 1.) -25 deg C, 2 h, 2.) r.t., 1 h

With sodium hydroxide; sodium tetrahydroborate; dimsylsodium; iodine; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; potassium iodide; In pyridine; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; benzene;
DOI:10.1016/S0040-4020(01)88649-X