(2RS,3R,4S)-6-benzylthiomethylene-2,3-dimethyl-4-tetrahydropyranyloxycyclohexanone

Base Information

• Chemical Name: (2RS,3R,4S)-6-benzylthiomethylene-2,3-dimethyl-4-tetrahydropyranyloxycyclohexanone
• CAS No.: 122169-37-3
• Molecular Formula: C₂₁H₂₈O₃S
• Molecular Weight: 360.518
• Mol file: 122169-37-3.mol

Synonyms:

Chemical Property of (2RS,3R,4S)-6-benzylthiomethylene-2,3-dimethyl-4-tetrahydropyranyloxycyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2RS,3R,4S)-6-benzylthiomethylene-2,3-dimethyl-4-tetrahydropyranyloxycyclohexanone

There total 12 articles about (2RS,3R,4S)-6-benzylthiomethylene-2,3-dimethyl-4-tetrahydropyranyloxycyclohexanone 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:

3,4-dihydro-2H-pyran (110-87-2) → (2RS,3R,4S)-6-benzylthiomethylene-2,3-dimethyl-4-tetrahydropyranyloxycyclohexanone (122169-37-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / p-TsOH / CH₂Cl₂ / Ambient temperature

2: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature

3: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C

4: 1.) p-TsCl / 1.) pyridine, 0 deg C, 3 h, 2.) pyridine, room temp.

With sodium hydride; p-toluenesulfonyl chloride; lithium diisopropyl amide; toluene-4-sulfonic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/S0040-4020(01)86136-6

Reference yield:

ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate (14160-65-7,77793-24-9,122090-88-4) → (2RS,3R,4S)-6-benzylthiomethylene-2,3-dimethyl-4-tetrahydropyranyloxycyclohexanone (122169-37-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 10 g / baker's yeast, sucrose / H₂O; ethanol / 30 °C

2: 4-N,N-dimethylaminopyridine / pyridine / Ambient temperature

3: 95 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

4: 87 percent / p-TsOH / CH₂Cl₂ / 3 h / Ambient temperature

5: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C

6: 83 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

7: 99 percent / Amberlite IR-120 / H₂O / 3 h / Heating

8: 90 percent / p-TsOH / CH₂Cl₂ / Ambient temperature

9: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature

10: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C

11: 1.) p-TsCl / 1.) pyridine, 0 deg C, 3 h, 2.) pyridine, room temp.

With N-Bromosuccinimide; lithium aluminium tetrahydride; baker's yeast; Amberlite IR-120; sodium hydride; p-toluenesulfonyl chloride; lithium diisopropyl amide; Sucrose; dmap; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; benzene;

DOI:10.1016/S0040-4020(01)86136-6

Reference yield:

(1S,2S)-4,4-ethylenedioxy-2-hydroxymethylcyclohexanol (96894-00-7) → (2RS,3R,4S)-6-benzylthiomethylene-2,3-dimethyl-4-tetrahydropyranyloxycyclohexanone (122169-37-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / p-TsOH / CH₂Cl₂ / 3 h / Ambient temperature

2: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C

3: 83 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

4: 99 percent / Amberlite IR-120 / H₂O / 3 h / Heating

5: 90 percent / p-TsOH / CH₂Cl₂ / Ambient temperature

6: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature

7: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C

8: 1.) p-TsCl / 1.) pyridine, 0 deg C, 3 h, 2.) pyridine, room temp.

With N-Bromosuccinimide; lithium aluminium tetrahydride; Amberlite IR-120; sodium hydride; p-toluenesulfonyl chloride; lithium diisopropyl amide; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; benzene;

DOI:10.1016/S0040-4020(01)86136-6

upstream raw materials:

phenylmethanethiol

3,4-dihydro-2H-pyran

ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

(1S,2S)-4,4-ethylenedioxy-2-hydroxymethylcyclohexanol

Downstream raw materials:

3-[(1R,2R,3R)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid methyl ester

3-[(1R,2R,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid methyl ester

3-[(1R,2R,3R)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid

(1'R,2'R,3'S)-3-(1',2'-dimethyl-6'-oxo-3'-tetrahydropyranyloxycyclohexane)propanoic acid

Refernces