(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-azetidin-2-one

Base Information

Chemical Name:(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-azetidin-2-one
CAS No.:132974-91-5
Molecular Formula:C₂₂H₂₉NO₂Si
Molecular Weight:367.563
Hs Code.:

Synonyms:(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-azetidin-2-one

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Chemical Property of (3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-azetidin-2-one

Chemical Property:

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Technology Process of (3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-azetidin-2-one

There total 13 articles about (3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-azetidin-2-one 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: 86.0%

: 132974-90-4
(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-1-(toluene-4-sulfonyl)-azetidin-2-one

: 132974-91-5
(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-azetidin-2-one

Guidance literature:: With Na-naphthalide; In 1,2-dimethoxyethane; at -78 ℃;
DOI:10.1016/0040-4039(91)80876-8

Reference yield:

: 132974-83-5
(5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one

: 132974-91-5
(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-azetidin-2-one

Guidance literature:: Multi-step reaction with 11 steps

1: 1) LiHMDS / 1) THF, -20 deg C, 10 min

2: 1) LiHMDS / 1) THF, -20 deg C, 20 min

3: H₂O₂ / tetrahydrofuran; H₂O

4: 75 percent / diethyl ether / -78 °C

5: 1) NaHMDS 2) trans-2-(phenylsulfonyl)-3-phenyloxaziridine / 1) THF, -78 deg C, 15 min

6: 90 percent / DIBAL / CH₂Cl₂ / -78 deg C to r.t.; or LiAlH₄, THF, 0 deg C to reflux

7: 55 percent / Pb(OAc)4 / benzene / 0.5 h

8: 100 percent / LiOH / tetrahydrofuran; H₂O / 0 °C

9: 93 percent / RuCl₃, NaIO₄ / CCl₄; acetonitrile; H₂O / 1.5 h / Ambient temperature

10: 76 percent / DCC, 4-pyrrolidinopyridine / CH₂Cl₂ / 2 h / Ambient temperature

11: 86 percent / Na-naphthalide / 1,2-dimethoxy-ethane / -78 °C

With lead(IV) acetate; ruthenium trichloride; lithium hydroxide; sodium periodate; Na-naphthalide; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-pyrrolidin-1-ylpyridine; N-(benzenesulfonyl)-3-phenyloxaziridine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; acetonitrile; benzene;
DOI:10.1016/0040-4039(91)80876-8

Reference yield:

: 132974-85-7
(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-1,5-dihydro-2H-pyrrol-2-one

: 132974-91-5
(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-azetidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 75 percent / diethyl ether / -78 °C

2: 1) NaHMDS 2) trans-2-(phenylsulfonyl)-3-phenyloxaziridine / 1) THF, -78 deg C, 15 min

3: 90 percent / DIBAL / CH₂Cl₂ / -78 deg C to r.t.; or LiAlH₄, THF, 0 deg C to reflux

4: 55 percent / Pb(OAc)4 / benzene / 0.5 h

5: 100 percent / LiOH / tetrahydrofuran; H₂O / 0 °C

6: 93 percent / RuCl₃, NaIO₄ / CCl₄; acetonitrile; H₂O / 1.5 h / Ambient temperature

7: 76 percent / DCC, 4-pyrrolidinopyridine / CH₂Cl₂ / 2 h / Ambient temperature

8: 86 percent / Na-naphthalide / 1,2-dimethoxy-ethane / -78 °C

With lead(IV) acetate; ruthenium trichloride; lithium hydroxide; sodium periodate; Na-naphthalide; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-pyrrolidin-1-ylpyridine; N-(benzenesulfonyl)-3-phenyloxaziridine; dicyclohexyl-carbodiimide; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; acetonitrile; benzene;
DOI:10.1016/0040-4039(91)80876-8