(2S,3R,5R)-3-Methyl-4,4,7-trioxo-3-phenylacetoxymethyl-6-[1-pyridin-2-yl-meth-(Z)-ylidene]-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,3R,5R)-3-Methyl-4,4,7-trioxo-3-phenylacetoxymethyl-6-[1-pyridin-2-yl-meth-(Z)-ylidene]-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 947589-56-2
• Molecular Formula: C₃₅H₃₀N₂O₇S
• Molecular Weight: 622.698

Synonyms:

Chemical Property of (2S,3R,5R)-3-Methyl-4,4,7-trioxo-3-phenylacetoxymethyl-6-[1-pyridin-2-yl-meth-(Z)-ylidene]-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5R)-3-Methyl-4,4,7-trioxo-3-phenylacetoxymethyl-6-[1-pyridin-2-yl-meth-(Z)-ylidene]-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 8 articles about (2S,3R,5R)-3-Methyl-4,4,7-trioxo-3-phenylacetoxymethyl-6-[1-pyridin-2-yl-meth-(Z)-ylidene]-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl 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:

benzhydryl 6-(allyloxycarbonylamino)penicillinate (121464-10-6) → (2S,3R,5R)-3-Methyl-4,4,7-trioxo-3-phenylacetoxymethyl-6-[1-pyridin-2-yl-meth-(Z)-ylidene]-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (947589-56-2)

Guidance literature:

Multi-step reaction with 7 steps

1: MCPBA

2: toluene / Heating

3: AgOAc

4: (n-Bu)3SnH, AcOH, Pd(PPh₃)4

5: 1.) Me₂CHONO, TFA, 2.) Rh(OAc)4, ethylene oxide

6: NaNH₂

7: MCPBA

With oxirane; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; i-propyl nitrite; tri-n-butyl-tin hydride; silver(I) acetate; sodium amide; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In toluene;

DOI:10.1016/S0960-894X(99)00325-X

Reference yield:

(2S,4S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (211623-24-4) → (2S,3R,5R)-3-Methyl-4,4,7-trioxo-3-phenylacetoxymethyl-6-[1-pyridin-2-yl-meth-(Z)-ylidene]-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (947589-56-2)

Guidance literature:

Multi-step reaction with 6 steps

1: toluene / Heating

2: AgOAc

3: (n-Bu)3SnH, AcOH, Pd(PPh₃)4

4: 1.) Me₂CHONO, TFA, 2.) Rh(OAc)4, ethylene oxide

5: NaNH₂

6: MCPBA

With oxirane; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; i-propyl nitrite; tri-n-butyl-tin hydride; silver(I) acetate; sodium amide; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In toluene;

DOI:10.1016/S0960-894X(99)00325-X

Reference yield:

6-aminopenicillanic acid diphenylmethyl ester (47547-28-4,78184-79-9) → (2S,3R,5R)-3-Methyl-4,4,7-trioxo-3-phenylacetoxymethyl-6-[1-pyridin-2-yl-meth-(Z)-ylidene]-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (947589-56-2)

Guidance literature:

Multi-step reaction with 8 steps

2: MCPBA

3: toluene / Heating

4: AgOAc

5: (n-Bu)3SnH, AcOH, Pd(PPh₃)4

6: 1.) Me₂CHONO, TFA, 2.) Rh(OAc)4, ethylene oxide

7: NaNH₂

8: MCPBA

With oxirane; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; i-propyl nitrite; tri-n-butyl-tin hydride; silver(I) acetate; sodium amide; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In toluene;

DOI:10.1016/S0960-894X(99)00325-X

upstream raw materials:

(2S,3R,5R)-3-Methyl-7-oxo-3-phenylacetoxymethyl-6-[1-pyridin-2-yl-meth-(Z)-ylidene]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

benzhydryl 6-(allyloxycarbonylamino)penicillinate

(R)-benzhydryl 2-((2R,3R)-3-(allyloxycarbonyl)amino-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate

(2S,4S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

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