(1R,6R,7aS)-allyl-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate

Base Information

• Chemical Name: (1R,6R,7aS)-allyl-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate
• CAS No.: 1440870-12-1
• Molecular Formula: C₂₉H₃₅NO₅S
• Molecular Weight: 509.667
• Mol file: 1440870-12-1.mol

Synonyms:(1R,6R,7aS)-allyl-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate

Chemical Property of (1R,6R,7aS)-allyl-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R,7aS)-allyl-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate

There total 29 articles about (1R,6R,7aS)-allyl-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate 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: 74.0%

(1R,6R,7aS)-allyl 6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-7a-(3-oxopropoxy)-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate → (1R,6R,7aS)-allyl-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate (1440870-12-1)

Guidance literature:

With pyrrolidine; acetic acid; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201207800

Reference yield:

(E)-methyl 3-[(2S,4R,5S)-5-allyl-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acrylate → (1R,6R,7aS)-allyl-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate (1440870-12-1)

Guidance literature:

Multi-step reaction with 24 steps

1.1: ozone / dichloromethane; methanol / 0.17 h / -78 °C / Inert atmosphere

2.1: sodium tetrahydroborate / dichloromethane; methanol / 2 h / -78 - 0 °C / Inert atmosphere

3.1: sodium tetrahydroborate; nickel dichloride / methanol / 2 h / 0 - 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphoranyl azide / toluene / 6 h / 0 - 80 °C / Inert atmosphere

5.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 4 h / 20 °C / Inert atmosphere

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

7.1: tributylphosphine / toluene / 2 h / 80 °C / Inert atmosphere

8.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 2 h / 20 °C / Inert atmosphere

9.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

10.1: 4-methyl-morpholine; tetra-n-propylammonium perruthenate. / dichloromethane / 1 h / 20 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

12.1: triethylamine / acetonitrile / 1 h / 20 °C / Inert atmosphere

13.1: (+)-10-camphorsulfonic acid / toluene / 0.67 h / 20 °C / Inert atmosphere

13.2: Inert atmosphere

14.1: acetic anhydride / pyridine / 0.67 h / 20 °C / Inert atmosphere

15.1: water; lithium hydroxide monohydrate / methanol / 2 h / 20 °C / Inert atmosphere

16.1: 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere

17.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

18.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

19.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 22 h / 20 °C / Inert atmosphere

20.1: C₁₀H₁₆NO; [bis(acetoxy)iodo]benzene / dichloromethane / 6 h / 0 °C / pH 7.2 / Inert atmosphere

21.1: potassium carbonate / acetone / 2 h / 20 °C / Inert atmosphere

22.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C / Inert atmosphere

23.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

24.1: acetic acid; pyrrolidine / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyrrolidine; 4-methyl-morpholine; 1H-imidazole; dmap; sodium tetrahydroborate; tetra-n-propylammonium perruthenate.; lithium hydroxide monohydrate; tributylphosphine; [bis(acetoxy)iodo]benzene; 10 wt% Pd(OH)2 on carbon; C₁₀H₁₆NO; (+)-10-camphorsulfonic acid; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; acetic anhydride; potassium carbonate; Dess-Martin periodane; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; isopropyl alcohol; acetone; toluene; acetonitrile; 7.1: |Aza-Wittig Reaction / 24.1: |Michael Addition;

DOI:10.1002/anie.201207800

Reference yield:

pentafluorophenyl 3-[(2S,4R,5S)-5-(2-azidoethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]propanoate → (1R,6R,7aS)-allyl-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate (1440870-12-1)

Guidance literature:

Multi-step reaction with 18 steps

1.1: tributylphosphine / toluene / 2 h / 80 °C / Inert atmosphere

2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 2 h / 20 °C / Inert atmosphere

3.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

4.1: 4-methyl-morpholine; tetra-n-propylammonium perruthenate. / dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

6.1: triethylamine / acetonitrile / 1 h / 20 °C / Inert atmosphere

7.1: (+)-10-camphorsulfonic acid / toluene / 0.67 h / 20 °C / Inert atmosphere

7.2: Inert atmosphere

8.1: acetic anhydride / pyridine / 0.67 h / 20 °C / Inert atmosphere

9.1: water; lithium hydroxide monohydrate / methanol / 2 h / 20 °C / Inert atmosphere

10.1: 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere

11.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

12.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

13.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 22 h / 20 °C / Inert atmosphere

14.1: C₁₀H₁₆NO; [bis(acetoxy)iodo]benzene / dichloromethane / 6 h / 0 °C / pH 7.2 / Inert atmosphere

15.1: potassium carbonate / acetone / 2 h / 20 °C / Inert atmosphere

16.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C / Inert atmosphere

17.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

18.1: acetic acid; pyrrolidine / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyrrolidine; 4-methyl-morpholine; 1H-imidazole; dmap; tetra-n-propylammonium perruthenate.; lithium hydroxide monohydrate; tributylphosphine; [bis(acetoxy)iodo]benzene; 10 wt% Pd(OH)2 on carbon; C₁₀H₁₆NO; (+)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; acetic anhydride; potassium carbonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; isopropyl alcohol; acetone; toluene; acetonitrile; 1.1: |Aza-Wittig Reaction / 18.1: |Michael Addition;

DOI:10.1002/anie.201207800

upstream raw materials:

(2S,4aS,10aR)-2-(4-methoxyphenyl)hexahydro-4H-[1,3]dioxino[5,4-d]azocin-8(9H)-one

(5R,6S)-5-hydroxy-6-(hydroxymethyl)azocan-2-one

(5R,6S)-6-[(tert-butyldiphenylsilyloxy)methyl]-5-hydroxyazocan-2-one

Downstream raw materials:

(1R,6R,7aS)-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylic acid