(S)-2-[(S)-1-Benzyl-2-(4-methoxymethylsulfanyl-piperidin-1-yl)-2-oxo-ethoxy]-hexanoic acid ((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-amide

Base Information

Chemical Name:(S)-2-[(S)-1-Benzyl-2-(4-methoxymethylsulfanyl-piperidin-1-yl)-2-oxo-ethoxy]-hexanoic acid ((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-amide
CAS No.:141048-01-3
Molecular Formula:C₃₆H₆₀N₂O₆S
Molecular Weight:648.948
Hs Code.:

(S)-2-[(S)-1-Benzyl-2-(4-methoxymethylsulfanyl-piperidin-1-yl)-2-oxo-ethoxy]-hexanoic acid ((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-amide

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Chemical Property of (S)-2-[(S)-1-Benzyl-2-(4-methoxymethylsulfanyl-piperidin-1-yl)-2-oxo-ethoxy]-hexanoic acid ((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-amide

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Technology Process of (S)-2-[(S)-1-Benzyl-2-(4-methoxymethylsulfanyl-piperidin-1-yl)-2-oxo-ethoxy]-hexanoic acid ((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-amide

There total 9 articles about (S)-2-[(S)-1-Benzyl-2-(4-methoxymethylsulfanyl-piperidin-1-yl)-2-oxo-ethoxy]-hexanoic acid ((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-amide 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:

: 5382-16-1
4-HYDROXYPIPERIDINE

: 141048-01-3
(S)-2-[(S)-1-Benzyl-2-(4-methoxymethylsulfanyl-piperidin-1-yl)-2-oxo-ethoxy]-hexanoic acid ((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-amide

Guidance literature:: Multi-step reaction with 8 steps

1: 16 h / Ambient temperature

2: 1.) (Ph)3P, diethyl azodicarboxylate (DEAD) / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 18 h

3: LiOH / tetrahydrofuran / 1.5 h / 5 °C

4: N,N-diisopropylethylemine / CH₂Cl₂ / Ambient temperature

5: KOH / H₂O / 24 h / Heating

6: 1.) 1-hydroxybenztriazole hydrate (HOBT), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -20 deg C, 2.) DMF, from -20 deg C to RT, overnight

7: 1.) NaH / 1.) THF, DMF, 45 deg C, 3 h, 2.) THF, 45 deg C , 45 min

8: 1.) 1-hydroxybenztriazole (HOBT), N-methylmorpholine, 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / 1.) DMF, -23 deg C, 2.) DMF, from -23 deg C to RT, 18 h

With 4-methyl-morpholine; potassium hydroxide; lithium hydroxide; sodium hydride; benzotriazol-1-ol; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jm00088a006

Reference yield:

: 141047-46-3
N-formyl-4-hydroxypiperidine

: 141048-01-3
(S)-2-[(S)-1-Benzyl-2-(4-methoxymethylsulfanyl-piperidin-1-yl)-2-oxo-ethoxy]-hexanoic acid ((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-amide

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) (Ph)3P, diethyl azodicarboxylate (DEAD) / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 18 h

2: LiOH / tetrahydrofuran / 1.5 h / 5 °C

3: N,N-diisopropylethylemine / CH₂Cl₂ / Ambient temperature

4: KOH / H₂O / 24 h / Heating

5: 1.) 1-hydroxybenztriazole hydrate (HOBT), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -20 deg C, 2.) DMF, from -20 deg C to RT, overnight

6: 1.) NaH / 1.) THF, DMF, 45 deg C, 3 h, 2.) THF, 45 deg C , 45 min

7: 1.) 1-hydroxybenztriazole (HOBT), N-methylmorpholine, 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / 1.) DMF, -23 deg C, 2.) DMF, from -23 deg C to RT, 18 h

With 4-methyl-morpholine; potassium hydroxide; lithium hydroxide; sodium hydride; benzotriazol-1-ol; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jm00088a006

Reference yield:

: 141048-05-7
4-Mercapto-piperidine-1-carbaldehyde

: 141048-01-3
(S)-2-[(S)-1-Benzyl-2-(4-methoxymethylsulfanyl-piperidin-1-yl)-2-oxo-ethoxy]-hexanoic acid ((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-amide

Guidance literature:: Multi-step reaction with 5 steps

1: N,N-diisopropylethylemine / CH₂Cl₂ / Ambient temperature

2: KOH / H₂O / 24 h / Heating

3: 1.) 1-hydroxybenztriazole hydrate (HOBT), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -20 deg C, 2.) DMF, from -20 deg C to RT, overnight

4: 1.) NaH / 1.) THF, DMF, 45 deg C, 3 h, 2.) THF, 45 deg C , 45 min

5: 1.) 1-hydroxybenztriazole (HOBT), N-methylmorpholine, 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / 1.) DMF, -23 deg C, 2.) DMF, from -23 deg C to RT, 18 h

With 4-methyl-morpholine; potassium hydroxide; sodium hydride; benzotriazol-1-ol; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; water;
DOI:10.1021/jm00088a006