(1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester
• CAS No.: 173105-10-7
• Molecular Formula: C₁₈H₂₀N₂O₆
• Molecular Weight: 360.367

Synonyms:(1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

Chemical Property of (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

There total 7 articles about (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic 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:

(3R,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-hydroxypropyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (161871-15-4) → (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.02,5]decane-6-carboxylic acid methyl ester (173105-10-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / Ambient temperature

2: 40 percent / FeCl₃ / benzene / 0.33 h / Heating

3: H₂, HOAc / Pd/C / methanol; tetrahydrofuran / 10 h / 2689.2 Torr

4: NaHCO₃ / methanol; tetrahydrofuran / 0.83 h / 0 - 5 °C

With hydrogen; iron(III) chloride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo951651u

Reference yield:

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amino}-butyric acid methyl ester (161871-11-0) → (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.02,5]decane-6-carboxylic acid methyl ester (173105-10-7)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂ / 1) -18 deg C, 2 h; 2) -10 --> 0 deg C, 30 min

2: 92 percent / trifluoroacetic acid / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 72 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / Ambient temperature

4: 40 percent / FeCl₃ / benzene / 0.33 h / Heating

5: H₂, HOAc / Pd/C / methanol; tetrahydrofuran / 10 h / 2689.2 Torr

6: NaHCO₃ / methanol; tetrahydrofuran / 0.83 h / 0 - 5 °C

With hydrogen; iron(III) chloride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo951651u

Reference yield:

(3R,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (161970-86-1) → (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.02,5]decane-6-carboxylic acid methyl ester (173105-10-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / trifluoroacetic acid / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 72 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / Ambient temperature

3: 40 percent / FeCl₃ / benzene / 0.33 h / Heating

4: H₂, HOAc / Pd/C / methanol; tetrahydrofuran / 10 h / 2689.2 Torr

5: NaHCO₃ / methanol; tetrahydrofuran / 0.83 h / 0 - 5 °C

With hydrogen; iron(III) chloride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo951651u

upstream raw materials:

(3R,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-hydroxypropyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amino}-butyric acid methyl ester

(3R,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

(1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

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