N-(benzyloxycarbonyl)-(3aR,4R,7aS)-4-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo-[4,5-c]pyridine

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Chemical Name:N-(benzyloxycarbonyl)-(3aR,4R,7aS)-4-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo-[4,5-c]pyridine
CAS No.:317809-54-4
Molecular Formula:C₂₅H₃₉NO₆Si
Molecular Weight:477.673
Hs Code.:

Synonyms:N-(benzyloxycarbonyl)-(3aR,4R,7aS)-4-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo-[4,5-c]pyridine

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Chemical Property of N-(benzyloxycarbonyl)-(3aR,4R,7aS)-4-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo-[4,5-c]pyridine

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Technology Process of N-(benzyloxycarbonyl)-(3aR,4R,7aS)-4-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo-[4,5-c]pyridine

There total 10 articles about N-(benzyloxycarbonyl)-(3aR,4R,7aS)-4-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo-[4,5-c]pyridine 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:

: 60410-16-4
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

: 317809-54-4
N-(benzyloxycarbonyl)-(3aR,4R,7aS)-4-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo-[4,5-c]pyridine

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / dimethylformamide; various solvent(s) / 0.5 h / 0 - 20 °C

1.2: 83 percent / PPh₃ / Pd(OAc)2 / dimethylformamide; various solvent(s) / 15 h

2.1: 98 percent / imidazole / dimethylformamide / 15 h / 20 °C

3.1: 95 percent / CH₂=CH₂ / PhCH=RuCl₂(PCy₃)2 / CH₂Cl₂ / 24 h / 20 °C

4.1: K₂CO₃; PhSH / dimethylformamide / 7 h / 20 - 45 °C

5.1: 642 mg / dimethylformamide / 20 °C

6.1: OsO₄; NMO / acetone; H₂O / 0 - 20 °C

7.1: pyridine; dimethyl-aminopyridine / CH₂Cl₂ / 48 h

8.1: 790 mg / pyridinium p-toluolsulfinate / 78 h

9.1: HCOOH / diethyl ether / 1 h

10.1: 37 mg / NaIO₄ / diethyl ether / 2 h

With pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; formic acid; N-methyl-2-indolinone; ethene; sodium hydride; potassium carbonate; thiophenol; pyridinium p-toluenesulfonite; Grubbs catalyst first generation; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1.1: deprotonation / 1.2: Alkylation / 2.1: silylation / 3.1: Rearrangement / 4.1: Hydrolysis / 5.1: Acylation / 6.1: hydroxylation / 7.1: tritylation / 8.1: Cyclization / 9.1: Elimination / 10.1: Elimination;
DOI:10.1021/ol000188r

Reference yield:

: 317809-48-6
N-but-3-enyl-N-((1R,4S)-4-hydroxy-cyclopent-2-enyl)-2-nitro-benzenesulfonamide

: 317809-54-4
N-(benzyloxycarbonyl)-(3aR,4R,7aS)-4-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo-[4,5-c]pyridine

Guidance literature:: Multi-step reaction with 9 steps

1: 98 percent / imidazole / dimethylformamide / 15 h / 20 °C

2: 95 percent / CH₂=CH₂ / PhCH=RuCl₂(PCy₃)2 / CH₂Cl₂ / 24 h / 20 °C

3: K₂CO₃; PhSH / dimethylformamide / 7 h / 20 - 45 °C

4: 642 mg / dimethylformamide / 20 °C

5: OsO₄; NMO / acetone; H₂O / 0 - 20 °C

6: pyridine; dimethyl-aminopyridine / CH₂Cl₂ / 48 h

7: 790 mg / pyridinium p-toluolsulfinate / 78 h

8: HCOOH / diethyl ether / 1 h

9: 37 mg / NaIO₄ / diethyl ether / 2 h

With pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; formic acid; N-methyl-2-indolinone; ethene; potassium carbonate; thiophenol; pyridinium p-toluenesulfonite; Grubbs catalyst first generation; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1: silylation / 2: Rearrangement / 3: Hydrolysis / 4: Acylation / 5: hydroxylation / 6: tritylation / 7: Cyclization / 8: Elimination / 9: Elimination;
DOI:10.1021/ol000188r

Reference yield:

: 317809-49-7
N-but-3-enyl-N-[(1R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl]-2-nitro-benzenesulfonamide

: 317809-54-4
N-(benzyloxycarbonyl)-(3aR,4R,7aS)-4-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo-[4,5-c]pyridine

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / CH₂=CH₂ / PhCH=RuCl₂(PCy₃)2 / CH₂Cl₂ / 24 h / 20 °C

2: K₂CO₃; PhSH / dimethylformamide / 7 h / 20 - 45 °C

3: 642 mg / dimethylformamide / 20 °C

4: OsO₄; NMO / acetone; H₂O / 0 - 20 °C

5: pyridine; dimethyl-aminopyridine / CH₂Cl₂ / 48 h

6: 790 mg / pyridinium p-toluolsulfinate / 78 h

7: HCOOH / diethyl ether / 1 h

8: 37 mg / NaIO₄ / diethyl ether / 2 h

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; formic acid; N-methyl-2-indolinone; ethene; potassium carbonate; thiophenol; pyridinium p-toluenesulfonite; Grubbs catalyst first generation; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1: Rearrangement / 2: Hydrolysis / 3: Acylation / 4: hydroxylation / 5: tritylation / 6: Cyclization / 7: Elimination / 8: Elimination;
DOI:10.1021/ol000188r