2,2-Dimethyl-propionic acid 2-oxo-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-acetoxymethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid 2-oxo-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-acetoxymethyl ester
• CAS No.: 164033-64-1
• Molecular Formula: C₂₂H₂₅NO₈S
• Molecular Weight: 463.508
• Mol file: 164033-64-1.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid 2-oxo-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-acetoxymethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid 2-oxo-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-acetoxymethyl ester

There total 6 articles about 2,2-Dimethyl-propionic acid 2-oxo-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-acetoxymethyl 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:

3-Methyl-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-but-2-enoic acid 2,2-dimethyl-propionyloxymethyl ester (164033-52-7) → 2,2-Dimethyl-propionic acid 2-oxo-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-acetoxymethyl ester (164033-64-1)

Guidance literature:

With ozone; In dichloromethane; at -78 ℃;

DOI:10.7164/antibiotics.48.399

Reference yield:

pivaloyloxy 6-oxopenicillanate (77819-78-4) → 2,2-Dimethyl-propionic acid 2-oxo-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-acetoxymethyl ester (164033-64-1)

Guidance literature:

Multi-step reaction with 5 steps

1: CH₂Cl₂ / 0 °C

2: H₂ / (Ph₃P)3RhCl / CH₂Cl₂; ethyl acetate / 2 h / 1520 Torr

3: PhHgCl, DBU / acetonitrile / Ambient temperature

4: acetonitrile

5: O₃ / CH₂Cl₂ / -78 °C

With hydrogen; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; phenylmercury(II) chloride; Wilkinson's catalyst; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.7164/antibiotics.48.399

Reference yield:

(2S,5R)-3,3-Dimethyl-7-oxo-6-[2-oxo-prop-(Z)-ylidene]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (84277-96-3) → 2,2-Dimethyl-propionic acid 2-oxo-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-acetoxymethyl ester (164033-64-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / (Ph₃P)3RhCl / CH₂Cl₂; ethyl acetate / 2 h / 1520 Torr

2: PhHgCl, DBU / acetonitrile / Ambient temperature

3: acetonitrile

4: O₃ / CH₂Cl₂ / -78 °C

With hydrogen; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; phenylmercury(II) chloride; Wilkinson's catalyst; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.7164/antibiotics.48.399

upstream raw materials:

3-Methyl-2-[(3R,4R)-2-oxo-3-(2-oxo-propyl)-4-phenylacetylsulfanyl-azetidin-1-yl]-but-2-enoic acid 2,2-dimethyl-propionyloxymethyl ester

pivaloyloxy 6-oxopenicillanate

Pivaloyloxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-oxo-propyl)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

(2S,5R)-3,3-Dimethyl-7-oxo-6-[2-oxo-prop-(Z)-ylidene]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester