tert-butyl (3R,5S)-3-tert-butyldiphenylsilyloxy-8-oxo-1-azaspiro[4.5]dec-6-ene-1-carboxylate

Base Information

Chemical Name:tert-butyl (3R,5S)-3-tert-butyldiphenylsilyloxy-8-oxo-1-azaspiro[4.5]dec-6-ene-1-carboxylate
CAS No.:479064-38-5
Molecular Formula:C₃₀H₃₉NO₄Si
Molecular Weight:505.729
Hs Code.:

Synonyms:tert-butyl (3R,5S)-3-tert-butyldiphenylsilyloxy-8-oxo-1-azaspiro[4.5]dec-6-ene-1-carboxylate

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Chemical Property of tert-butyl (3R,5S)-3-tert-butyldiphenylsilyloxy-8-oxo-1-azaspiro[4.5]dec-6-ene-1-carboxylate

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Technology Process of tert-butyl (3R,5S)-3-tert-butyldiphenylsilyloxy-8-oxo-1-azaspiro[4.5]dec-6-ene-1-carboxylate

There total 7 articles about tert-butyl (3R,5S)-3-tert-butyldiphenylsilyloxy-8-oxo-1-azaspiro[4.5]dec-6-ene-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:

: 3-(tert-butyl-diphenyl-silanyloxy)-6-methanesulfonyloxy-8-oxo-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

: 479064-38-5
tert-butyl (3R,5S)-3-tert-butyldiphenylsilyloxy-8-oxo-1-azaspiro[4.5]dec-6-ene-1-carboxylate

Guidance literature:: With silica gel; In hexane; ethyl acetate;
DOI:10.1016/S0040-4020(02)01292-9

Reference yield:

: 226225-51-0
2-but-3-enyl-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 479064-38-5
tert-butyl (3R,5S)-3-tert-butyldiphenylsilyloxy-8-oxo-1-azaspiro[4.5]dec-6-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / DIBAH / toluene / 2 h / -78 °C

2: 93 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

3: 92 percent / CuCl; PdCl₂; oxygen / dimethylformamide; H₂O / 5 h / 20 °C

4: 80 percent / KOH / ethanol / 1.5 h / 0 °C

5: Et₃N / CH₂Cl₂ / 0 - 20 °C

6: 578 mg / silica gel / hexane; ethyl acetate

With potassium hydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve; oxygen; silica gel; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; copper(l) chloride; palladium dichloride; In ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 3: Wacker oxidation;
DOI:10.1016/S0040-4020(02)01292-9

Reference yield:

: 226225-42-9
(2S,4R)-N-tert-butyloxycarbonyl-4-[(tert-butyldiphenylsilyl)oxy]pyrrolidine-2-carboxylic acid methyl ester

: 479064-38-5
tert-butyl (3R,5S)-3-tert-butyldiphenylsilyloxy-8-oxo-1-azaspiro[4.5]dec-6-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 67 percent / LDA; HMPA / tetrahydrofuran / -78 °C

2: 86 percent / DIBAH / toluene / 2 h / -78 °C

3: 93 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

4: 92 percent / CuCl; PdCl₂; oxygen / dimethylformamide; H₂O / 5 h / 20 °C

5: 80 percent / KOH / ethanol / 1.5 h / 0 °C

6: Et₃N / CH₂Cl₂ / 0 - 20 °C

7: 578 mg / silica gel / hexane; ethyl acetate

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve; oxygen; silica gel; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; copper(l) chloride; palladium dichloride; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 4: Wacker oxidation;
DOI:10.1016/S0040-4020(02)01292-9