(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone

Base Information

• Chemical Name: (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone
• CAS No.: 158150-46-0
• Molecular Formula: C₂₃H₂₅NO₅
• Molecular Weight: 395.455
• Mol file: 158150-46-0.mol

Synonyms:(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone

Chemical Property of (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone

There total 7 articles about (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-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: 78.0%

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxo-3-phenyliodoniopropyl>-2-azetidinone (187280-57-5,158150-43-7) → (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone (158150-46-0)

Guidance literature:

In ethanol; for 0.333333h; Heating;

DOI:10.1016/S0040-4020(96)01093-9

Reference yield:

(R)-4-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-oxo-pentanoic acid benzhydryl ester (161683-27-8) → (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone (158150-46-0)

Guidance literature:

With hydrogenchloride; In acetonitrile; for 1h;

DOI:10.1016/S0040-4020(96)01093-9

Reference yield:

1,1-Diphenylmethanol (91-01-0) → (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone (158150-46-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂

2: 89 percent / zinc, cupric bromide / tetrahydrofuran / 1.5 h / 25 - 30 °C

3: 87 percent / dicyclohexylcarbodiimide, pyridine, trifluoroacetic acid, dimethyl sulfoxide / toluene / 3.5 h / Ambient temperature; other reagents: pyridinium chlorochromate; sodium dichromate; 1.) dimethyl sulfoxide, trifluoroacetic anhydride, 2.) triethylamine or triethylamine/trimethylsilyl chloride

4: 2.82 g / hydrochloric acid / acetonitrile / 1 h

With pyridine; hydrogenchloride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; copper(ll) bromide; zinc; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

DOI:10.1016/S0040-4020(96)01093-9

upstream raw materials:

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxo-3-phenyliodoniopropyl>-2-azetidinone

(R)-4-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-oxo-pentanoic acid benzhydryl ester

1,1-Diphenylmethanol

4(R)-<1-buten-3(S)-yl>-3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxoazetidine

Downstream raw materials:

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxo-3-phenyliodoniopropyl>-2-azetidinone

diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

diphenylmethyl (2S,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate

diphenylmethyl (2R,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate