(3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-methyl ester

Base Information

• Chemical Name: (3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-methyl ester
• CAS No.: 1145983-10-3
• Molecular Formula: C₁₈H₁₇NO₃S₂
• Molecular Weight: 359.47
• Mol file: 1145983-10-3.mol

Synonyms:(3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-methyl ester

Chemical Property of (3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-methyl ester

There total 5 articles about (3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-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: 75.0%

carbon disulfide (75-15-0,12122-00-8) + (-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone (146924-91-6,194234-97-4) + methyl iodide (74-88-4) → (3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-methyl ester (1145983-10-3)

Guidance literature:

(-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone; With sodium hydride; In tetrahydrofuran; at 20 ℃; Cooling;

carbon disulfide; at 0 ℃; for 1.5h;

methyl iodide; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.tet.2008.11.042

Reference yield:

[4-(benzylideneamino)phenyl]methanol (783-08-4) → (3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-methyl ester (1145983-10-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 12 h / -78 - 20 °C

2.1: Lipase PS Amano enzyme / aq. phosphate buffer / pH 7.2 / Resolution of racemate; Enzymatic reaction

3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 20 °C

3.2: 1.5 h / 0 °C

3.3: 3 h / 0 - 20 °C

With sodium hydride; triethylamine; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; mineral oil;

Reference yield:

cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one (186613-02-5) → (3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-methyl ester (1145983-10-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Lipase PS Amano enzyme / aq. phosphate buffer / pH 7.2 / Resolution of racemate; Enzymatic reaction

2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 20 °C

2.2: 1.5 h / 0 °C

2.3: 3 h / 0 - 20 °C

With sodium hydride; In tetrahydrofuran; aq. phosphate buffer; mineral oil;

upstream raw materials:

carbon disulfide

(-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone

methyl iodide

[4-(benzylideneamino)phenyl]methanol

Downstream raw materials:

(S)-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one

(S)-4-phenyl-2-azetidinone

(S)-2-oxo-4-phenyl-azetidine-1-carboxylic acid tert-butyl ester

S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester

Refernces

• 1、 -. "Process for preparation of enantiomerically pure S-(+)-N, N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine". Paragraph 0089; 0090; 0091. . Retrieved 2014/07/09.