<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone

Base Information

• Chemical Name: <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone
• CAS No.: 82008-55-7
• Molecular Formula: C₂₂H₃₅NO₅Si
• Molecular Weight: 421.609

Synonyms:<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone

Chemical Property of <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone

Chemical Property:

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Technology Process of <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone

There total 13 articles about <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone 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:

<3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylic acid (81902-54-7) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone (82008-55-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / 4-dimethylaminopyridine / dimethylformamide / 18 h / 20 - 25 °C

2: 18.7 g / oxalyl chloride / tetrahydrofuran / 3 h / 25 °C

3: 1.) CdCl₂ / 1.) 1 h, 24 deg C, THF 2.) 2 h, 25 deg C, THF

With dmap; oxalyl dichloride; cadmium(II) chloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)91966-0

Reference yield:

diethyl N-(2,4-dimethoxybenzyl)-amino-malonate (81902-49-0) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone (82008-55-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / triethylamine / tetrahydrofuran / 15 h / 20 °C

2: 95.9 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature

3: 62 percent / 1N NaOH / pyridine / 5 °C

5: 89 percent / 4-dimethylaminopyridine / dimethylformamide / 18 h / 20 - 25 °C

6: 18.7 g / oxalyl chloride / tetrahydrofuran / 3 h / 25 °C

7: 1.) CdCl₂ / 1.) 1 h, 24 deg C, THF 2.) 2 h, 25 deg C, THF

With dmap; sodium hydroxide; oxalyl dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; cadmium(II) chloride; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)91966-0

Reference yield:

<3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylic acid (81902-57-0) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone (82008-55-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 18.7 g / oxalyl chloride / tetrahydrofuran / 3 h / 25 °C

2: 1.) CdCl₂ / 1.) 1 h, 24 deg C, THF 2.) 2 h, 25 deg C, THF

With oxalyl dichloride; cadmium(II) chloride; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)91966-0

upstream raw materials:

methylmagnesium bromide

<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylic acid chloride

<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylic acid

diethyl N-(2,4-dimethoxybenzyl)-amino-malonate

Downstream raw materials:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

(3S,4R)-4-benzenesulfonyl-3-((1R)-1-(tert-butyldimethylsilanyloxy)-ethyl)-azetidin-2-one

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