{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1R,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester

Base Information

Chemical Name:{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1R,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester
CAS No.:299177-89-2
Molecular Formula:C₂₉H₅₁NO₇Si₂
Molecular Weight:581.897
Hs Code.:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1R,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester

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Chemical Property of {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1R,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester

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Technology Process of {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1R,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester

There total 10 articles about {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1R,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester 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:

: 74503-07-4
allyl oxalyl chloride

: 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

: 299177-89-2
{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1R,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1016/S0040-4020(00)00413-0

Reference yield:

: 1655-07-8
ethyl 2-oxocyclohexane carboxylate

: 299177-89-2
{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1R,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester

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: 7.73 g / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With dipyridinium dichromate; baker's yeast; 4 A molecular sieve; triethylamine; zinc(II) chloride; lithium hexamethyldisilazane; Sucrose; In tetrahydrofuran; dichloromethane; water; 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: Acylation;
DOI:10.1016/S0040-4020(00)00413-0

Reference yield:

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

: 299177-89-2
{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1R,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester

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: 7.73 g / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With dmap; dipyridinium dichromate; 4 A molecular sieve; triethylamine; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1.1: silylation / 2.1: Oxidation / 3.1: deprotonation / 3.2: silylation / 4.1: Condensation / 4.2: desilylation / 5.1: Acylation;
DOI:10.1016/S0040-4020(00)00413-0