3-[(1R,2S,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester

Base Information

• Chemical Name: 3-[(1R,2S,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester
• CAS No.: 142459-44-7
• Molecular Formula: C₃₀H₄₉NO₆
• Molecular Weight: 519.722

Synonyms:

Chemical Property of 3-[(1R,2S,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(1R,2S,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester

There total 53 articles about 3-[(1R,2S,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propionic 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:

(E)-(4R,5S)-4-Acetoxy-5-(methanesulfonyloxy)-2-hexenal (142459-13-0) → 3-[(1R,2S,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester (142459-44-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h

2: methanol / 9.5 h / 5 °C

3: imidazole / dimethylformamide / 1 h / Ambient temperature

4: 93 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

5: 83 percent / Bu₄NF / tetrahydrofuran

6: 1) NaH / 1) THF 2) r.t., 1 h

7: 99 percent / DIBALH / hexane; diethyl ether / 0.08 h

8: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -80 deg C - 60 deg C, 1 h, 2) - 40 deg C, 30 min

9: NaClO₂, 2-methyl-2-butene, NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol / 0.33 h / Ambient temperature

10: 142 mg / diethyl ether

11: 1.23 g / LDA / tetrahydrofuran; hexane / 0.58 h / -100 °C

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo00036a026

Reference yield:

3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid (124908-71-0) → 3-[(1R,2S,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester (142459-44-7)

Guidance literature:

Multi-step reaction with 15 steps

1: diethyl ether

2: 8.28 g / DIBALH / hexane; diethyl ether / 1.5 h / -50 °C

3: 12.4 g / imidazole / CH₂Cl₂ / 0.25 h

4: 1) 2,6-di-tert-butylcresol, dichloromaleic anhydride 2) NaOMe / 1) chlorobenzene, 150 deg C, 24 h 2) MeOH, 0 deg C, 50 min

5: HF / acetonitrile / 1 h / 0 °C / Resolution: 1) isooctane, benzene, (Ac)2O, Amano lipase CES on Celite, 23 deg C, 5 h, 2) chromatography (silica gel, AcOEt/hexane), 3) recrystallization (Et₂O)

6: 99 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

7: 69 percent / 1) lithium hexamethyldisilazane, 2) HMPA / 1) THF, hexane, -50 deg C - -60 deg C, 1 h, 2) -35 deg C, 24 h

8: 98 percent / NH₂OH*HCl, pyridine / CH₂Cl₂ / 15 h / Heating

9: 1) TsCl, DMAP, pyridine, 2) LiCl, MeOH / 1) CH₂Cl₂, -80 deg C - r.t., 1 h, 2) r.t., 2 weeks

10: 72 percent / H₂ / 10percent Pd/C / ethanol

11: ethanol / 1.5 h / Heating

12: 627 mg / catecholborane, NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 48 h / Heating

13: 473 mg / 5percent HF / acetonitrile / 0.75 h / 0 °C

14: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -80 deg C - -60 deg C, 1 h, 2) -60 deg C, 50 min

15: 1.23 g / LDA / tetrahydrofuran; hexane / 0.58 h / -100 °C

With pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dichloromaleic acid anhydride; oxalyl dichloride; 2,4-di-t-butyl-3-methyl phenol; hydrogen fluoride; hydroxylamine hydrochloride; hydrogen; sodium methylate; sodium acetate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; lithium chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/jo00036a026

Reference yield:

(3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol (142459-32-3) → 3-[(1R,2S,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester (142459-44-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 12.4 g / imidazole / CH₂Cl₂ / 0.25 h

2: 1) 2,6-di-tert-butylcresol, dichloromaleic anhydride 2) NaOMe / 1) chlorobenzene, 150 deg C, 24 h 2) MeOH, 0 deg C, 50 min

3: HF / acetonitrile / 1 h / 0 °C / Resolution: 1) isooctane, benzene, (Ac)2O, Amano lipase CES on Celite, 23 deg C, 5 h, 2) chromatography (silica gel, AcOEt/hexane), 3) recrystallization (Et₂O)

4: 99 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

5: 69 percent / 1) lithium hexamethyldisilazane, 2) HMPA / 1) THF, hexane, -50 deg C - -60 deg C, 1 h, 2) -35 deg C, 24 h

6: 98 percent / NH₂OH*HCl, pyridine / CH₂Cl₂ / 15 h / Heating

7: 1) TsCl, DMAP, pyridine, 2) LiCl, MeOH / 1) CH₂Cl₂, -80 deg C - r.t., 1 h, 2) r.t., 2 weeks

8: 72 percent / H₂ / 10percent Pd/C / ethanol

9: ethanol / 1.5 h / Heating

10: 627 mg / catecholborane, NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 48 h / Heating

11: 473 mg / 5percent HF / acetonitrile / 0.75 h / 0 °C

12: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -80 deg C - -60 deg C, 1 h, 2) -60 deg C, 50 min

13: 1.23 g / LDA / tetrahydrofuran; hexane / 0.58 h / -100 °C

With pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dichloromaleic acid anhydride; oxalyl dichloride; 2,4-di-t-butyl-3-methyl phenol; hydrogen fluoride; hydroxylamine hydrochloride; hydrogen; sodium methylate; sodium acetate; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; lithium chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/jo00036a026

upstream raw materials:

(R)-1-((S)-5-Methoxy-tetrahydro-furan-2-yl)-ethanol

(R)-6-Hydroxymethyl-3-methyl-tetrahydro-pyran-2-one

(R)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)butyric acid

(R)-2,2-Dimethyl-1,3-dioxolane-4-butanoic acid, methyl ester

Downstream raw materials:

(Z)-3-[(1R,2R,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester

C₄₁H₆₈O₈Si

4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one

3-((R)-2-{(1R,2R,6S)-2-[(E)-3-Hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propenyl]-6-methyl-cyclohexyl}-propionyl)-4-methoxy-5-methylene-5H-furan-2-one

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