[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetic acid methyl ester

Base Information

• Chemical Name: [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetic acid methyl ester
• CAS No.: 81902-67-2
• Molecular Formula: C₂₃H₃₇NO₆Si
• Molecular Weight: 451.635
• Mol file: 81902-67-2.mol

Synonyms:

Chemical Property of [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetic acid methyl ester

There total 12 articles about [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetic acid methyl 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: 67.0%

<3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-diazoacetyl-2-azetidinone (81902-64-9) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetic acid methyl ester (81902-67-2)

Guidance literature:

In methanol; Irradiation;

DOI:10.1016/S0040-4039(01)92460-8

Reference yield:

(2,4-dimethoxy-benzylamino)-acetic acid (20839-79-6) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetic acid methyl ester (81902-67-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / DCC / tetrahydrofuran / 0.25 h / 20 °C

2: LiN(SiMe₃)2 / 1. THF, 0 grad C, 15 min; 2. 20 grad C

3: 77 percent / CF₃COOH / CH₂Cl₂ / 2 h / 25 °C

4: 4-dimethylaminopyridine / dimethylformamide

5: (COCl)2 / tetrahydrofuran / 2 h / 25 °C

6: 73 percent / diethyl ether

7: 67 percent / methanol / Irradiation

With dmap; oxalyl dichloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)92460-8

Reference yield:

<3S-<3α(S*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylate (80829-72-7) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetic acid methyl ester (81902-67-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / CF₃COOH / CH₂Cl₂ / 2 h / 25 °C

2: 4-dimethylaminopyridine / dimethylformamide

3: (COCl)2 / tetrahydrofuran / 2 h / 25 °C

4: 73 percent / diethyl ether

5: 67 percent / methanol / Irradiation

With dmap; oxalyl dichloride; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)92460-8

upstream raw materials:

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

(2,4-dimethoxy-benzylamino)-acetic acid

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

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