N-((1S,4S,4aS,5R,6R,8aS)-5-amino-4-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6-hydroxy-1,6-dimethyldecahydronaphthalen-1-yl)-4-methylbenzenesulfonamide

Base Information

• Chemical Name: N-((1S,4S,4aS,5R,6R,8aS)-5-amino-4-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6-hydroxy-1,6-dimethyldecahydronaphthalen-1-yl)-4-methylbenzenesulfonamide
• CAS No.: 1354928-50-9
• Molecular Formula: C₂₇H₄₃ClN₂O₄S
• Molecular Weight: 527.168

Synonyms:N-((1S,4S,4aS,5R,6R,8aS)-5-amino-4-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6-hydroxy-1,6-dimethyldecahydronaphthalen-1-yl)-4-methylbenzenesulfonamide

Chemical Property of N-((1S,4S,4aS,5R,6R,8aS)-5-amino-4-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6-hydroxy-1,6-dimethyldecahydronaphthalen-1-yl)-4-methylbenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((1S,4S,4aS,5R,6R,8aS)-5-amino-4-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6-hydroxy-1,6-dimethyldecahydronaphthalen-1-yl)-4-methylbenzenesulfonamide

There total 25 articles about N-((1S,4S,4aS,5R,6R,8aS)-5-amino-4-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6-hydroxy-1,6-dimethyldecahydronaphthalen-1-yl)-4-methylbenzenesulfonamide 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: 83.0%

C27H41ClN2O4S (1354928-74-7) → N-((1S,4S,4aS,5R,6R,8aS)-5-amino-4-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6-hydroxy-1,6-dimethyldecahydronaphthalen-1-yl)-4-methylbenzenesulfonamide (1354928-50-9)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at 0 - 40 ℃; for 1.5h;

DOI:10.1039/c1cc16468f

Reference yield:

(2S,3R,6R)-2-{3-(benzyloxy)propyl}-6-(tert-butyldiphenylsilyloxy)-3,7-dimethyloct-7-ene-1,3-diol (440333-58-4) → N-((1S,4S,4aS,5R,6R,8aS)-5-amino-4-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6-hydroxy-1,6-dimethyldecahydronaphthalen-1-yl)-4-methylbenzenesulfonamide (1354928-50-9)

Guidance literature:

Multi-step reaction with 22 steps

1.1: pyridine / 3 h / 20 °C

1.2: 24 h / 60 °C

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 48 h / 60 °C

3.1: 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine / dichloromethane / 0.08 h / 0 °C

4.1: diisobutylaluminium hydride / hexane; toluene / 0.17 h / -78 °C

5.1: pyridine / 0.5 h / 20 °C

6.1: iodonium(di-γ-collidine) perchlorate / dichloromethane / 4 h / 20 °C

7.1: triethyl borane; tri-n-butyl-tin hydride / tetrahydrofuran / 1 h / -78 °C

8.1: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C

9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.17 h / 20 °C

10.1: tetrahydrofuran / 0.17 h / 0 °C

11.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C

12.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.17 h / -78 °C

13.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

14.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

14.2: 2 h / -78 - 20 °C

15.1: tetrabutyl ammonium fluoride / 2 h / 20 °C

16.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

17.1: disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C

18.1: sodium azide; ammonium chloride / methanol; water / 10 h / Reflux

19.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C

20.1: copper(II) bis(trifluoromethanesulfonate) / acetonitrile / 3 h / 20 °C / Molecular sieve

21.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / tetrahydrofuran; methanol / 3.17 h / 0 - 20 °C

22.1: lithium triethylborohydride / tetrahydrofuran / 1.5 h / 0 - 40 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; disodium hydrogenphosphate; n-butyllithium; sodium azide; nickel(II) chloride hexahydrate; 1,1,1,3,3,3-hexachloro-propan-2-one; triethyl borane; iodonium(di-γ-collidine) perchlorate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; copper(II) bis(trifluoromethanesulfonate); diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 16.1: intramolecular Diels-Alder reaction;

DOI:10.1039/c1cc16468f

Reference yield:

(2E,6R)-(+)-3,7-dimethyl-octa-2,7-diene-1,6-diol (440333-15-3) → N-((1S,4S,4aS,5R,6R,8aS)-5-amino-4-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6-hydroxy-1,6-dimethyldecahydronaphthalen-1-yl)-4-methylbenzenesulfonamide (1354928-50-9)

Guidance literature:

Multi-step reaction with 27 steps

1.1: dmap; triethylamine / 1,2-dichloro-ethane / 1 h / 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C

3.1: pyridinium p-toluenesulfonate / methanol / 9 h / 20 °C

4.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane / 1 h / -20 °C / Molecular sieve

5.1: copper(l) iodide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

5.2: 3 h / -78 - 20 °C / Inert atmosphere

6.1: pyridine / 3 h / 20 °C

6.2: 24 h / 60 °C

7.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 48 h / 60 °C

8.1: 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine / dichloromethane / 0.08 h / 0 °C

9.1: diisobutylaluminium hydride / hexane; toluene / 0.17 h / -78 °C

10.1: pyridine / 0.5 h / 20 °C

11.1: iodonium(di-γ-collidine) perchlorate / dichloromethane / 4 h / 20 °C

12.1: triethyl borane; tri-n-butyl-tin hydride / tetrahydrofuran / 1 h / -78 °C

13.1: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C

14.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.17 h / 20 °C

15.1: tetrahydrofuran / 0.17 h / 0 °C

16.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C

17.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.17 h / -78 °C

18.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

19.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

19.2: 2 h / -78 - 20 °C

20.1: tetrabutyl ammonium fluoride / 2 h / 20 °C

21.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

22.1: disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C

23.1: sodium azide; ammonium chloride / methanol; water / 10 h / Reflux

24.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C

25.1: copper(II) bis(trifluoromethanesulfonate) / acetonitrile / 3 h / 20 °C / Molecular sieve

26.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / tetrahydrofuran; methanol / 3.17 h / 0 - 20 °C

27.1: lithium triethylborohydride / tetrahydrofuran / 1.5 h / 0 - 40 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; copper(l) iodide; n-butyllithium; sodium azide; nickel(II) chloride hexahydrate; 1,1,1,3,3,3-hexachloro-propan-2-one; diethyl (2S,3S)-tartrate; triethyl borane; iodonium(di-γ-collidine) perchlorate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; copper(II) bis(trifluoromethanesulfonate); diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: Sharpless asymmetric epoxidation / 21.1: intramolecular Diels-Alder reaction;

DOI:10.1039/c1cc16468f

upstream raw materials:

C₂₄H₃₆O₆

(2S,3R,6R)-3-acetoxy-2-(3-benzyloxypropyl)-6-chloro-3,7-dimethyl-7-octenyl acetate

(1aR,3aR,7S,7aR,7bS)-7-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-1a-methyl-octahydronaphtho[2,1-b]oxiren-4(7bH)-one

C₁₉H₃₁ClO₂

Downstream raw materials:

kalihinol-A

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