(3R,4S)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-azetidin-2-one
• CAS No.: 260354-47-0
• Molecular Formula: C₂₉H₃₁NO₅
• Molecular Weight: 473.569
• Mol file: 260354-47-0.mol

Synonyms:(3R,4S)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-azetidin-2-one

Chemical Property of (3R,4S)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-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)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-azetidin-2-one

There total 6 articles about (3R,4S)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-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: 50.0%

Benzyl-[1-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-amine (1025887-95-9) + S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate (139007-45-7) → (3R,4S)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-azetidin-2-one (260354-47-0)

Guidance literature:

DOI:10.1021/jo990964c

Reference yield:

3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3) → (3R,4S)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-azetidin-2-one (260354-47-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / K₂OsO₂(OH)4; (DHQ)2-PHAL; K₃Fe(CN)6 / K₂CO₃; methanesulfonamide / H₂O; 2-methyl-propan-2-ol / 20 °C

2: 85 percent / p-TsOH*H₂O / benzene / 1 h / Heating

3: DIBAL / toluene / 2 h / -78 °C

4: CH₂Cl₂ / 1 h / 0 °C

5: Et₃N / CH₂Cl₂ / -78 - 20 °C

With potassium dioxotetrahydroxoosmate(VI); (DHQ)2-PHAL; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In dichloromethane; water; toluene; tert-butyl alcohol; benzene; 1: Sharpless AD reaction / 2: Cycloaddition / 3: Reduction / 4: Condensation / 5: Cycloaddition;

DOI:10.1021/jo990964c

Reference yield:

Benzyl-[1-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-amine (1025887-95-9) + Benzyloxyacetyl chloride (19810-31-2) → (3S,4R)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-azetidin-2-one + (3R,4S)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-azetidin-2-one (260354-47-0)

Guidance literature:

With triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo990964c

upstream raw materials:

Benzyl-[1-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-amine

Benzyloxyacetyl chloride

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

3-(4-methoxy-phenyl)acrylic acid methyl ester

Downstream raw materials:

(2S,3R)-2-{(S)-2-Benzylamino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

(2S,3R)-2-{(S)-2-Amino-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetylamino}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

(S)-3-Benzyl-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxazolidine-2,5-dione

(+)-(3R,4R)-cis-1-benzyl-3-benzyloxy-4-formyl-2-azetidinone