(3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one
• CAS No.: 149706-06-9
• Molecular Formula: C₂₄H₂₇NO₃
• Molecular Weight: 377.483
• Mol file: 149706-06-9.mol

Synonyms:(3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one

Chemical Property of (3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one

There total 5 articles about (3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)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:

(+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone (149818-33-7) → (3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one (149706-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / aq. NaIO₄ / ethyl acetate / 4 h / 50 °C

2: n-BuLi / hexane; tetrahydrofuran / Ambient temperature

With sodium periodate; n-butyllithium; In tetrahydrofuran; hexane; ethyl acetate;

DOI:10.1021/jo00069a048

Reference yield:

[(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine (141781-23-9) → (3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one (149706-06-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) TiCl₄, TEA / 1.) CH₂Cl₂, -78 deg C, 30 min., 2.) CH₂Cl₂, 0 deg C, 5 h

2: TFA / H₂O / Ambient temperature

3: 100 percent / aq. NaIO₄ / ethyl acetate / 4 h / 50 °C

4: n-BuLi / hexane; tetrahydrofuran / Ambient temperature

With sodium periodate; n-butyllithium; TEA; titanium tetrachloride; trifluoroacetic acid; In tetrahydrofuran; hexane; water; ethyl acetate;

DOI:10.1021/jo00069a048

Reference yield:

S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate (139007-45-7) → (3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one (149706-06-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) TiCl₄, TEA / 1.) CH₂Cl₂, -78 deg C, 30 min., 2.) CH₂Cl₂, 0 deg C, 5 h

2: TFA / H₂O / Ambient temperature

3: 100 percent / aq. NaIO₄ / ethyl acetate / 4 h / 50 °C

4: n-BuLi / hexane; tetrahydrofuran / Ambient temperature

With sodium periodate; n-butyllithium; TEA; titanium tetrachloride; trifluoroacetic acid; In tetrahydrofuran; hexane; water; ethyl acetate;

DOI:10.1021/jo00069a048

upstream raw materials:

cyclohexyl(triphenyl)phosphonium bromide

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone

(+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone

S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate

Downstream raw materials:

(3R,4S)-4-(Cyclohexylmethyl)-1-(4-methoxyphenyl)-3-triisopropylsilyloxy-2-azetidinone

(3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-one