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

Base Information

Chemical Name:(3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(2R,6R)-2-(hydroxymethyl)cyclohexanon-6-yl]azetidin-2-one
CAS No.:211945-46-9
Molecular Formula:C₁₈H₃₃NO₄Si
Molecular Weight:355.55
Hs Code.:

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

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Chemical Property of (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(2R,6R)-2-(hydroxymethyl)cyclohexanon-6-yl]azetidin-2-one

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Technology Process of (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(2R,6R)-2-(hydroxymethyl)cyclohexanon-6-yl]azetidin-2-one

There total 10 articles about (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(2R,6R)-2-(hydroxymethyl)cyclohexanon-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: 74.0%

: 135297-29-9
(3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(t-butyldimethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

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

Guidance literature:: With ammonium bifluoride; In N,N-dimethyl-formamide; at 20 ℃; for 72h;
DOI:10.1016/S0040-4020(00)00413-0

Reference yield:

: 1655-07-8
ethyl 2-oxocyclohexane carboxylate

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

Guidance literature:: Multi-step reaction with 5 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

With 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;
DOI:10.1016/S0040-4020(00)00413-0

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With 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;
DOI:10.1016/S0040-4020(00)00413-0