(3R,4S)-cis-1-(p-anisyl)-3-(mesyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-cis-1-(p-anisyl)-3-(mesyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• CAS No.: 115828-88-1
• Molecular Formula: C₁₆H₂₁NO₇S
• Molecular Weight: 371.411
• Mol file: 115828-88-1.mol

Synonyms:(3R,4S)-cis-1-(p-anisyl)-3-(mesyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Chemical Property of (3R,4S)-cis-1-(p-anisyl)-3-(mesyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-cis-1-(p-anisyl)-3-(mesyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

There total 5 articles about (3R,4S)-cis-1-(p-anisyl)-3-(mesyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 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: 95.0%

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-87-0) + methanesulfonyl chloride (124-63-0) → (3R,4S)-cis-1-(p-anisyl)-3-(mesyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-88-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00253a013

Reference yield:

(3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1-(4-methoxyphenyl)azetidin-2-one (115857-84-6) → (3R,4S)-cis-1-(p-anisyl)-3-(mesyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-88-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / HCOONH₄ / Pd/C / methanol / 0.5 h / Heating

2: 88 percent / Et₃N / CH₂Cl₂ / 2 h / -10 - 20 °C

With ammonium formate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1055/s-2005-872263

Reference yield:

N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine (103239-04-9) → (3R,4S)-cis-1-(p-anisyl)-3-(mesyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-88-1)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / CH₂Cl₂ / Ambient temperature

2: 100 percent / H₂ / 10percent Pd/C / ethanol / 8 h / 2327.2 Torr / Ambient temperature

3: 95 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

With dmap; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/jo00253a013

upstream raw materials:

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

methanesulfonyl chloride

(3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1-(4-methoxyphenyl)azetidin-2-one

[1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine

Downstream raw materials:

(3S,4S)-trans-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

(3S,4R)-trans-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

(4S)-1-(p-anisyl)-3-iodo-4-[(S)-2',2'-dimethyl-1',3'-dioxalan-4-yl]azetidin-2-one

Methanesulfonic acid (2S,3R)-2-((S)-1,2-dihydroxy-ethyl)-1-(4-methoxy-phenyl)-4-oxo-azetidin-3-yl ester