(3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(triethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

Base Information

Chemical Name:(3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(triethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one
CAS No.:256642-02-1
Molecular Formula:C₂₄H₄₇NO₄Si₂
Molecular Weight:469.812
Hs Code.:

Synonyms:(3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(triethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

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Chemical Property of (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(triethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

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Technology Process of (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(triethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

There total 11 articles about (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(triethylsilyloxymethyl)cyclohexanone-6'-yl]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: 98.0%

: 994-30-9
triethylsilyl chloride

: 211945-46-9
(3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(2R,6R)-2-(hydroxymethyl)cyclohexanon-6-yl]azetidin-2-one

: 256642-02-1
(3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(triethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 2.5h;
DOI:10.1016/S0040-4020(00)00413-0

Reference yield:

: 1655-07-8
ethyl 2-oxocyclohexane carboxylate

: 256642-02-1
(3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(triethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: baker's yeast; sucrose / H₂O / 1 h / 30 °C

1.2: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

1.3: 4-DMAP; Et₃N / CH₂Cl₂ / 19 h / 20 °C

2.1: 88 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 4.5 h / 20 °C

3.1: lithiumhexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

3.2: 100 percent / tetrahydrofuran / -78 - 20 °C

4.1: ZnCl₂ / CH₂Cl₂ / 3 h / 20 °C

4.2: 63 percent / SiO₂ / methanol / 20 °C

5.1: 74 percent / ammonium hydrogen fluoride / dimethylformamide / 72 h / 20 °C

6.1: 98 percent / imidazole / dimethylformamide / 2.5 h / 0 °C

With 1H-imidazole; dipyridinium dichromate; baker's yeast; ammonium bifluoride; 4 A molecular sieve; zinc(II) chloride; lithium hexamethyldisilazane; Sucrose; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Reduction / 1.2: Reduction / 1.3: silylation / 2.1: Oxidation / 3.1: deprotonation / 3.2: silylation / 4.1: Condensation / 4.2: desilylation / 5.1: desilylation / 6.1: silylation;
DOI:10.1016/S0040-4020(00)00413-0

Reference yield:

: 51606-50-9
(1R,2R)-2-(hydroxymethyl)cyclohexanol

: 256642-02-1
(3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(triethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 20 °C

2.1: 88 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 4.5 h / 20 °C

3.1: lithiumhexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

3.2: 100 percent / tetrahydrofuran / -78 - 20 °C

4.1: ZnCl₂ / CH₂Cl₂ / 3 h / 20 °C

4.2: 63 percent / SiO₂ / methanol / 20 °C

5.1: 74 percent / ammonium hydrogen fluoride / dimethylformamide / 72 h / 20 °C

6.1: 98 percent / imidazole / dimethylformamide / 2.5 h / 0 °C

With 1H-imidazole; dmap; dipyridinium dichromate; ammonium bifluoride; 4 A molecular sieve; triethylamine; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Oxidation / 3.1: deprotonation / 3.2: silylation / 4.1: Condensation / 4.2: desilylation / 5.1: desilylation / 6.1: silylation;
DOI:10.1016/S0040-4020(00)00413-0