benzyl (3^*R,4^*S)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-2-(2,2-dimethyl-1,3-dioxan-5-ylidene)acetate

Base Information

• Chemical Name: benzyl (3^*R,4^*S)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-2-(2,2-dimethyl-1,3-dioxan-5-ylidene)acetate
• CAS No.: 90602-94-1
• Molecular Formula: C₂₆H₂₈N₂O₆S
• Molecular Weight: 496.584
• Mol file: 90602-94-1.mol

Synonyms:benzyl (3^*R,4^*S)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-2-(2,2-dimethyl-1,3-dioxan-5-ylidene)acetate

Chemical Property of benzyl (3^*R,4^*S)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-2-(2,2-dimethyl-1,3-dioxan-5-ylidene)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (3^*R,4^*S)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-2-(2,2-dimethyl-1,3-dioxan-5-ylidene)acetate

There total 6 articles about benzyl (3^*R,4^*S)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-2-(2,2-dimethyl-1,3-dioxan-5-ylidene)acetate 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:

(5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol (53104-32-8) → benzyl (3*R,4*S)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-2-(2,2-dimethyl-1,3-dioxan-5-ylidene)acetate (90602-94-1)

Guidance literature:

Multi-step reaction with 6 steps

1: KH₂PO₄, NaIO₄ / H₂O / 4 h, 10 deg C, 5 h, 20 deg C

2: 69 percent / potassium tert.-butoxide / tetrahydrofuran / <-60 deg C, 30 min; 0 deg C, 30 min

3: 64 percent / triethyl amine, Lawesson reagent / 1,2-dimethoxy-ethane / 0.33 h / 20 °C

4: lithium 2-propoxide / tetrahydrofuran / 1.75 h / 20 °C

5: 84 percent / triethyl amine / CH₂Cl₂ / 12 h / 20 °C

6: 1) triethyl amine, hydrogen sulfide, 2) pyridine / 1) dichloromethane, 0 deg C, 4 h, 2) -20 deg C, 8 h

With Lawessons reagent; pyridine; sodium periodate; potassium dihydrogenphosphate; hydrogen sulfide; potassium tert-butylate; lithium isopropoxide; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water;

DOI:10.1016/0040-4020(89)80098-5

Reference yield:

2,2,-dimethyl-1,3-dioxan-5-one (74181-34-3) → benzyl (3*R,4*S)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-2-(2,2-dimethyl-1,3-dioxan-5-ylidene)acetate (90602-94-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 69 percent / potassium tert.-butoxide / tetrahydrofuran / <-60 deg C, 30 min; 0 deg C, 30 min

2: 64 percent / triethyl amine, Lawesson reagent / 1,2-dimethoxy-ethane / 0.33 h / 20 °C

3: lithium 2-propoxide / tetrahydrofuran / 1.75 h / 20 °C

4: 84 percent / triethyl amine / CH₂Cl₂ / 12 h / 20 °C

5: 1) triethyl amine, hydrogen sulfide, 2) pyridine / 1) dichloromethane, 0 deg C, 4 h, 2) -20 deg C, 8 h

With Lawessons reagent; pyridine; hydrogen sulfide; potassium tert-butylate; lithium isopropoxide; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1016/0040-4020(89)80098-5

Reference yield:

benzyl 2-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2-formylamino-acetate (90602-90-7) → benzyl (3*R,4*S)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-2-(2,2-dimethyl-1,3-dioxan-5-ylidene)acetate (90602-94-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / triethyl amine, Lawesson reagent / 1,2-dimethoxy-ethane / 0.33 h / 20 °C

2: lithium 2-propoxide / tetrahydrofuran / 1.75 h / 20 °C

3: 84 percent / triethyl amine / CH₂Cl₂ / 12 h / 20 °C

4: 1) triethyl amine, hydrogen sulfide, 2) pyridine / 1) dichloromethane, 0 deg C, 4 h, 2) -20 deg C, 8 h

With Lawessons reagent; pyridine; hydrogen sulfide; lithium isopropoxide; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1016/0040-4020(89)80098-5

upstream raw materials:

benzoyl chloride

(5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol

2,2,-dimethyl-1,3-dioxan-5-one

benzyl 2-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2-formylamino-acetate

Downstream raw materials:

Trifluoro-acetic acid (2R,3R)-3-benzoylamino-1-(4-hydroxymethyl-2-oxo-2,5-dihydro-furan-3-yl)-4-oxo-azetidin-2-yl ester

(1'R^*,5'S^*)-3-(7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-ene-6-yl)-4-acetoxymethyl-2,5-dihydrofuran-7-one

(3-Benzoylamino-2-chloro-4-oxo-azetidin-1-yl)-(2,2-dimethyl-[1,3]dioxan-5-ylidene)-acetic acid benzyl ester

(3R^*,4S^*)-3-benzoylamino-1-(4-hydroxymethyl-2-oxo-2,5-dihydrofuran-3-yl)-4-methylthio-azetidin-2-one