(1'S,4'S,4a'S,5'R,6'R,8a'S)-5'-azido-4'-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6'-methyl-1-tosyloctahydro-2'H-spiro[aziridine-2,1'-naphthalen]-6'-ol

Base Information

Chemical Name:(1'S,4'S,4a'S,5'R,6'R,8a'S)-5'-azido-4'-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6'-methyl-1-tosyloctahydro-2'H-spiro[aziridine-2,1'-naphthalen]-6'-ol
CAS No.:1354928-48-5
Molecular Formula:C₂₇H₃₉ClN₄O₄S
Molecular Weight:551.15
Hs Code.:

(1'S,4'S,4a'S,5'R,6'R,8a'S)-5'-azido-4'-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6'-methyl-1-tosyloctahydro-2'H-spiro[aziridine-2,1'-naphthalen]-6'-ol

Synonyms:(1'S,4'S,4a'S,5'R,6'R,8a'S)-5'-azido-4'-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6'-methyl-1-tosyloctahydro-2'H-spiro[aziridine-2,1'-naphthalen]-6'-ol

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Chemical Property of (1'S,4'S,4a'S,5'R,6'R,8a'S)-5'-azido-4'-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6'-methyl-1-tosyloctahydro-2'H-spiro[aziridine-2,1'-naphthalen]-6'-ol

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Technology Process of (1'S,4'S,4a'S,5'R,6'R,8a'S)-5'-azido-4'-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6'-methyl-1-tosyloctahydro-2'H-spiro[aziridine-2,1'-naphthalen]-6'-ol

There total 21 articles about (1'S,4'S,4a'S,5'R,6'R,8a'S)-5'-azido-4'-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6'-methyl-1-tosyloctahydro-2'H-spiro[aziridine-2,1'-naphthalen]-6'-ol 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:

: C₂₅H₃₈ClIO₄

: 1354928-48-5
(1'S,4'S,4a'S,5'R,6'R,8a'S)-5'-azido-4'-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6'-methyl-1-tosyloctahydro-2'H-spiro[aziridine-2,1'-naphthalen]-6'-ol

Guidance literature:: Multi-step reaction with 14 steps

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

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

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

4.1: tetrahydrofuran / 0.17 h / 0 °C

5.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C

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

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

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

8.2: 2 h / -78 - 20 °C

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

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

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

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

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

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

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; n-butyllithium; sodium azide; triethyl borane; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; copper(II) bis(trifluoromethanesulfonate); diisobutylaluminium hydride; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 10.1: intramolecular Diels-Alder reaction;
DOI:10.1039/c1cc16468f

Reference yield:

: 158512-40-4
(E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-1,6-dien-3-ol

: 1354928-48-5
(1'S,4'S,4a'S,5'R,6'R,8a'S)-5'-azido-4'-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6'-methyl-1-tosyloctahydro-2'H-spiro[aziridine-2,1'-naphthalen]-6'-ol

Guidance literature:: Multi-step reaction with 24 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C

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

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

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

4.2: 3 h / -78 - 20 °C / Inert atmosphere

5.1: pyridine / 3 h / 20 °C

5.2: 24 h / 60 °C

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

7.1: 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine / dichloromethane / 0.08 h / 0 °C

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

9.1: pyridine / 0.5 h / 20 °C

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

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

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

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

14.1: tetrahydrofuran / 0.17 h / 0 °C

15.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C

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

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

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

18.2: 2 h / -78 - 20 °C

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

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

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

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

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

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

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; copper(l) iodide; n-butyllithium; sodium azide; 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; 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; 3.1: Sharpless asymmetric epoxidation / 20.1: intramolecular Diels-Alder reaction;
DOI:10.1039/c1cc16468f

Reference yield:

: 440333-27-7
C₄₀H₅₄O₆Si

: 1354928-48-5
(1'S,4'S,4a'S,5'R,6'R,8a'S)-5'-azido-4'-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6'-methyl-1-tosyloctahydro-2'H-spiro[aziridine-2,1'-naphthalen]-6'-ol

Guidance literature:: Multi-step reaction with 19 steps

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

2.1: 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine / dichloromethane / 0.08 h / 0 °C

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

4.1: pyridine / 0.5 h / 20 °C

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

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

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

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

9.1: tetrahydrofuran / 0.17 h / 0 °C

10.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C

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

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

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

13.2: 2 h / -78 - 20 °C

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

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

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

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

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

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

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; n-butyllithium; sodium azide; 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; 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; 15.1: intramolecular Diels-Alder reaction;
DOI:10.1039/c1cc16468f