(3S,4S)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one

Base Information

• Chemical Name: (3S,4S)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one
• CAS No.: 842172-36-5
• Molecular Formula: C₂₅H₂₆INO₅
• Molecular Weight: 547.39
• Mol file: 842172-36-5.mol

Synonyms:(3S,4S)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one

Chemical Property of (3S,4S)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one

There total 9 articles about (3S,4S)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-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:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (3S,4S)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one (842172-36-5)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / acetone / 3 h / 0 - 20 °C

2: NaN₃ / 12 h / 0 - 20 °C

3: toluene / 4 h / Heating

4: toluene; benzene / 12 h / 20 °C

5: Et₃N / CH₂Cl₂ / 12 h / 20 °C

With sodium azide; triethylamine; In dichloromethane; acetone; toluene; benzene;

DOI:10.1055/s-2004-834890

Reference yield:

Phenoxyacetyl chloride (701-99-5) + [1-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(E)-ylidene]-((E)-3-phenyl-allyl)-amine (842172-35-4) → (3R,4R)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one (842172-37-6) + (3S,4S)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one (842172-36-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1055/s-2004-834890

Reference yield:

alpha-D-glucopyranose (492-62-6) → (3S,4S)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one (842172-36-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 32 percent / ZnCl₂; H₃PO₄ / 30 h / 20 °C

2: 69 percent / PPh₃; I₂; imidazole / toluene / 17 h / Heating

3: 76 percent / aq. H₂SO₄ / methanol / 6 h / 20 °C

4: 90 percent / NaIO₄/SiO₂ / CH₂Cl₂ / 1 h / 20 °C

5: toluene; benzene / 12 h / 20 °C

6: Et₃N / CH₂Cl₂ / 12 h / 20 °C

With 1H-imidazole; sodium periodate; phosphoric acid; sulfuric acid; iodine; silica gel; triethylamine; triphenylphosphine; zinc(II) chloride; In methanol; dichloromethane; toluene; benzene;

DOI:10.1055/s-2004-834890

upstream raw materials:

Phenoxyacetyl chloride

[1-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(E)-ylidene]-((E)-3-phenyl-allyl)-amine

alpha-D-glucopyranose

3-deoxy-3-iodo-1,2:5,6-di-O-isopropylidene-α-D-allofuranose