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

Base Information

• Chemical Name: [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-1-oxiranyl-ethyl)-4-oxo-azetidin-1-yl]-hydroxy-acetic acid 4-nitro-benzyl ester
• CAS No.: 123108-00-9
• Molecular Formula: C₂₄H₃₆N₂O₈Si
• Molecular Weight: 508.644
• Mol file: 123108-00-9.mol

Synonyms:

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

There total 9 articles about [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-1-oxiranyl-ethyl)-4-oxo-azetidin-1-yl]-hydroxy-acetic acid 4-nitro-benzyl 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:

(3S,4R)-3-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-4-(1-methyl-2-propynyl)-2-azetidinone (615252-63-6) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-1-oxiranyl-ethyl)-4-oxo-azetidin-1-yl]-hydroxy-acetic acid 4-nitro-benzyl ester (123108-00-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) LDA / 1) THF, hexane, -78 to -40 deg C, 1 h, 2) THF, hexane, -78 deg C to RT then RT, overnight

2: 97 percent / K₂CO₃ / methanol / 5.5 h / Ambient temperature

3: 99 percent / hydrogen, quinoline / 5percent Pd-BaSO₄ / methanol / 0.17 h / Ambient temperature

4: Et₃N / benzene / Heating; Dean-Stark trap with mol. sieves 4A

5: m-CPBA, NaHCO₃ / CH₂Cl₂ / Ambient temperature

With quinoline; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on barium sulfate; In methanol; dichloromethane; benzene;

DOI:10.1248/cpb.37.2338

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-1-oxiranyl-ethyl)-4-oxo-azetidin-1-yl]-hydroxy-acetic acid 4-nitro-benzyl ester (123108-00-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) TMSOTf, 2) KF / 1) CH₂Cl₂, 0 deg C, 15 min then 14 h, RT, 2) ether, H₂O, 1 h; var. reag.: BF₃*Et₂O

2: 99 percent / hydrogen, quinoline / 5percent Pd-BaSO₄ / methanol / 0.17 h / Ambient temperature

3: Et₃N / benzene / Heating; Dean-Stark trap with mol. sieves 4A

4: m-CPBA, NaHCO₃ / CH₂Cl₂ / Ambient temperature

With quinoline; potassium fluoride; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on barium sulfate; In methanol; dichloromethane; benzene;

DOI:10.1248/cpb.37.2338

Reference yield:

(3R,4R)-3-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-4-<(1S)-1-methyl-2-propynyl>-2-azetidinone (113396-81-9) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-1-oxiranyl-ethyl)-4-oxo-azetidin-1-yl]-hydroxy-acetic acid 4-nitro-benzyl ester (123108-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / hydrogen, quinoline / 5percent Pd-BaSO₄ / methanol / 0.17 h / Ambient temperature

2: Et₃N / benzene / Heating; Dean-Stark trap with mol. sieves 4A

3: m-CPBA, NaHCO₃ / CH₂Cl₂ / Ambient temperature

With quinoline; hydrogen; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on barium sulfate; In methanol; dichloromethane; benzene;

DOI:10.1248/cpb.37.2338

upstream raw materials:

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

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

p-nitrobenzyl glyoxylate

(3R,4R)-3-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-4-<(1S)-1-methyl-2-propynyl>-2-azetidinone

Downstream raw materials:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(R)-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(R)-2-hydroxy-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-propyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

(4S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester