N-{(1S,2S,3S,6R)-2-[2-((2R,4R)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl}-2,2-dimethyl-butyramide

Base Information

• Chemical Name: N-{(1S,2S,3S,6R)-2-[2-((2R,4R)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl}-2,2-dimethyl-butyramide
• CAS No.: 135716-27-7
• Molecular Formula: C₂₄H₄₃NO₄
• Molecular Weight: 409.61
• Mol file: 135716-27-7.mol

Synonyms:N-{(1S,2S,3S,6R)-2-[2-((2R,4R)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl}-2,2-dimethyl-butyramide

Chemical Property of N-{(1S,2S,3S,6R)-2-[2-((2R,4R)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl}-2,2-dimethyl-butyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{(1S,2S,3S,6R)-2-[2-((2R,4R)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl}-2,2-dimethyl-butyramide

There total 14 articles about N-{(1S,2S,3S,6R)-2-[2-((2R,4R)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl}-2,2-dimethyl-butyramide 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: 95.0%

[(4R,6R)-6-(2-{(1S,2S,3R,6S)-2-[(2,2-Dimethyl-butyrylamino)-methyl]-6-methyl-3-propyl-cyclohexyl}-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester (136598-09-9) → N-{(1S,2S,3S,6R)-2-[2-((2R,4R)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl}-2,2-dimethyl-butyramide (135716-27-7)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1016/0040-4039(91)80587-V

Reference yield:

[(1S,2S,3S,6R)-2-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3-methyl-6-propyl-cyclohexyl]-methanol (135716-23-3) → N-{(1S,2S,3S,6R)-2-[2-((2R,4R)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl}-2,2-dimethyl-butyramide (135716-27-7)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: NaN₃ / dimethylformamide / 50 °C

3: H₂, Et₃N / 10percent Pd-C / ethanol; methanol

4: 76 percent / DMAP / pyridine

5: n-Bu₄NF / tetrahydrofuran

6: 1) Dess-Martin periodinane, 2) 1.0 aq. KMnO₄, 5percent NaH₂PO₄ / t-BuOH, CH₂Cl₂

7: 78 percent / diethyl ether / 0 °C

8: 95 percent / aq. HF / acetonitrile

With dmap; potassium permanganate; sodium dihydrogenphosphate; sodium azide; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(91)80587-V

Reference yield:

[(1S,2S,3S,6S)-6-Allyl-2-(2-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3-methyl-cyclohexyl]-methanol (135716-19-7) → N-{(1S,2S,3S,6R)-2-[2-((2R,4R)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl}-2,2-dimethyl-butyramide (135716-27-7)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / 10percent Pd-C / methanol

2: Et₃N / CH₂Cl₂ / 0 °C

3: NaN₃ / dimethylformamide / 50 °C

4: H₂, Et₃N / 10percent Pd-C / ethanol; methanol

5: 76 percent / DMAP / pyridine

6: n-Bu₄NF / tetrahydrofuran

7: 1) Dess-Martin periodinane, 2) 1.0 aq. KMnO₄, 5percent NaH₂PO₄ / t-BuOH, CH₂Cl₂

8: 78 percent / diethyl ether / 0 °C

9: 95 percent / aq. HF / acetonitrile

With dmap; potassium permanganate; sodium dihydrogenphosphate; sodium azide; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(91)80587-V

upstream raw materials:

[(4R,6R)-6-(2-{(1S,2S,3R,6S)-2-[(2,2-Dimethyl-butyrylamino)-methyl]-6-methyl-3-propyl-cyclohexyl}-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester

2,2-dimethylbutanoyl chloride

N-((1S,2S,3S,6R)-2-{2-[(4R,6S)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl)-2,2-dimethyl-butyramide

[(4R,6R)-6-(2-{(1S,2S,3R,6S)-2-[(2,2-Dimethyl-butyrylamino)-methyl]-6-methyl-3-propyl-cyclohexyl}-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid

Downstream raw materials:

[1S-[1α(βS*,δS*),2β,3α,6α]]-2-[[(2,2-Dimethyl-1-oxobutyl)amino]methyl]-β,δ-dihydroxy-6-methyl-3-propylcyclohexaneheptanoic acid, monolithium salt