tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate

Base Information

Chemical Name:tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate
CAS No.:237421-67-9
Molecular Formula:C₃₃H₄₅NO₇Si
Molecular Weight:595.808
Hs Code.:

Synonyms:tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate

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Chemical Property of tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate

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Technology Process of tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate

There total 6 articles about tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate 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: 61.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 237421-66-8
tert-butyl (2S,4R)-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate

: 237421-67-9
tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate

Guidance literature:: With dmap; triethylamine; In 1,4-dioxane; at 85 ℃;
DOI:10.1016/S0040-4020(99)00403-2

Reference yield:

: 91229-91-3
tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

: 237421-67-9
tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate

Guidance literature:: Multi-step reaction with 6 steps

1: 29.5 percent / lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 °C

2: 62 percent / 1M HCl / ethyl acetate / 4 h / Ambient temperature

3: 89 percent / K₃Fe(CN)6, K₂CO₃, OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / Ambient temperature

4: 75 percent / DMAP, Et₃N / CH₂Cl₂ / 19 h / Ambient temperature

5: 95 percent / tetrapropylammonium perruthenate, N-methylmorpholine-N-oxide, 4 Angstroem MS / CH₂Cl₂ / 2 h / Ambient temperature

6: 61 percent / DMAP, Et₃N / dioxane / 85 °C

With hydrogenchloride; dmap; osmium(VIII) oxide; tetrapropylammonium perruthennate; 4 Angstroem MS; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; lithium hexamethyldisilazane; potassium hexacyanoferrate(III); In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1016/S0040-4020(99)00403-2

Reference yield:

: 237421-63-5
tert-butyl (2S,4R)-4-(prop-2-enyl)-pyroglutamate

: 237421-67-9
tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / K₃Fe(CN)6, K₂CO₃, OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / Ambient temperature

2: 75 percent / DMAP, Et₃N / CH₂Cl₂ / 19 h / Ambient temperature

3: 95 percent / tetrapropylammonium perruthenate, N-methylmorpholine-N-oxide, 4 Angstroem MS / CH₂Cl₂ / 2 h / Ambient temperature

4: 61 percent / DMAP, Et₃N / dioxane / 85 °C

With dmap; osmium(VIII) oxide; tetrapropylammonium perruthennate; 4 Angstroem MS; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); In 1,4-dioxane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4020(99)00403-2